Control of kinetics and thermodynamics of [1,5]-shifts by aromaticity: A view through the prism of Marcus theory

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9329-9342

  Alabugin, Igor V ^a   Manoharan, Mariappan ^a   Breiner, Boris ^a   Lewis, Frederick D ^b  

^a FLORIDA STATE UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CHEMICAL ANALYSIS; REACTION KINETICS;

AROMATICITY;

AROMATIC COMPOUNDS;

AROMATIC HYDROCARBON;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENERGY; KINETICS; MAGNETISM; REACTION ANALYSIS; THEORY; THERMODYNAMICS;

EID: 0042208364     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035729x     Document Type: Article

References (217)

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2. (b) Isaacs, N. Physical Organic Chemistry; Longman: Essex, 1995.
3. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
4. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
5. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
6. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
7. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
8. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
9. For early reports of this reaction, see: (a) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2077. (b) Mironov, V. A.; Sobolev, E. V.; Elizarova, A. N. Dokl. Akad. SSSR 1962, 143, 1112. (c) Hydrogen [1,5]-shifts in cycloheptatrienes: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Proc. Chem. Soc. 1962, 359. (d) Transannular hydrogen [1,5]-shifts: ter Borg, A. P.; Kloosterziel, H.; Van Meurs, N. Recl. Trav. Chim. 1963, 82, 717. (e) Hydrogen [1,5]-shift in cyclic trienes and homotrienes: Glass, D. S.; Zirner, J.; Winstein, S. Proc. Chem. Soc. 1963, 276, Hydrogen [1,5]-shift in cyclopentadiene: (f) McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329. (g) Sigmatropic rearrangements in trimethylcyclopentadienes: de Haan, J. W.; Kloosterziel, H. Rec. Trav. Chim. 1968, 87, 298.
10. Theoretical analysis of sigmatropic reactions and discovery of selection rules: (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781. (d) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
11. Theoretical analysis of sigmatropic reactions and discovery of selection rules: (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781. (d) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
12. Theoretical analysis of sigmatropic reactions and discovery of selection rules: (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781. (d) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
13. Theoretical analysis of sigmatropic reactions and discovery of selection rules: (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781. (d) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
14. Theoretical analysis of sigmatropic reactions and discovery of selection rules: (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511. (b) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970. (c) Hoffmann, R.; Woodward, R. B. Acc. Chem. Res. 1968, 1, 17. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781. (d) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
15. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
16. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
17. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
18. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
19. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
20. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
21. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
22. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
23. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
24. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
25. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
26. Hydrogen [1,5]-shift in cyclopentadiene and indene: (a) Roth, W. R. Tetrahedron Lett. 1964, 1009. (b) Thermal hydrogen [1,5]-shift in cycloheptatrienes: de Dobbelaere, J. R.; Mironov, V. A.; Chizhov, O. S.; Kimelfeld, Ya. M.; Akhrem, A. A. Tetrahedron Lett. 1969, 499. (c) Dienyl and homodienyl hydrogen [1,5]-shift: Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999. (d) Kinetics of the hydrogen [1,5]-shift in the gas phase: Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688. (e) Hydrogen [1,5]-shift in deuterated polycyclics: Pomerantz, M.; Gruber, G. W. J. Org. Chem. 1968, 33, 4501. (f) Thermal rearrangements in 3,4-benzotropolidene: Gruber, G. W.; Pomerantz, M. Tetrahedron Lett. 1970, 43, 3755. (g) Naphthalene formation from 1,2-benzotropilidene: Pomerantz, M.; Ross, A. S.; Gruber, G. W. J. Am. Chem. Soc. 1972, 94, 1403. (h) Stereochemistry and kinetics in the hydrogen [1,5]-shift: Roth, W. R.; Konig, J.; Stein, K. Chem. Ber. 1970, 103, 426. (i) Geometric details in hydrogen [1,5]-shifts, deuterium isotope effects: Kwart, H.; Brechbiel, M. W.; Acheson, R. M.; Ward, D. C. J. Am. Chem. Soc. 1982, 104, 4671. (j) Hydrogen [1,5]-shift and trapping experiments in 1,2,5,6-dibenzotropilidene: Pomerantz, M.; Fink, R. J. Org. Chem. 1977, 42, 2788. (k) Sigmatropic rearrangements in squarates: Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627. (l) Kinetic studies and activation parameters on the thermal hydrogen [1,5]-shift in deuterated cyclooctadienes: Baldwin, J. E.; Leber, P. A.; Lee, T. W. J. Org. Chem. 2001, 66, 5269.
27. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
28. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
29. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
30. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
31. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
32. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
33. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
34. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
35. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
36. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
37. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and
38. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
39. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
40. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
41. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
42. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
43. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
44. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
45. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
46. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
47. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
48. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
49. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
50. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
51. (a) [1,5]-Chlorine shifts: Looker, J. J. J. Org. Chem. 1972, 37, 1059. (b) Hydrogen [1,5]-shift in cyclic dienes and trienes: Dedobbelaere, J. R.; van Zeeventer, E. L.; de Haan, J. W.; Buck, H. M. Theor. Chim. Acta 1975, 38, 241. (c) Transition state calculations on the hydrogen [1,5]-shift: Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185. (d) Ab initio study on the hydrogen [1,5]-shift: Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519. (e) Tunneling in hydrogen [1,5]-shifts: Dewar, M. J. S.; Merz, K. M., Jr.; Stewart, J. P. J. Chem. Soc., Chem. Commun. 1985, 166. (f) Mechanistic study of hydrogen [1,5]-shifts: Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253. Earlier ab initio studies on the transition states of sigmatropic rearrangements: (g) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. (THEOCHEM) 1986, 136, 121. (h) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139. (i) Dewar, M. J. S.; Healy, E. F.; Ruiz, J. M. J. Am. Chem. Soc. 1988, 110, 2666. (j) Kinetic isotope effect in the hydrogen [1,5]-shift through molecular modeling: Liu, Y.-P.; Lynch, G. C.; Truong, T. N.; Lu, D.-H.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 2408. (k) [1,5]-Hydrogen shift in cyclopentadiene, pyrrole, and phosphole: Bachrach, S. M. J. Org. Chem. 1993, 58, 5414. (l) [1,5]-Hydrogen shifts in tetrazole: Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465. (m) Experimental study on reaction kinetics of hydrogen [1,3]- and [1,5]-shifts: Arai, T.; Tobita, S.; Shizuka, H. Chem. Phys. Lett. 1994, 223, 521. (n) Laser flash photolysis study of hydrogen [1,3]- and [1,5]-shifts and tunneling effects therein: Arai, T.; Tobita, S.; Shizuka, H. J. Am. Chem. Soc. 1995, 117, 3968. (o) The allene effect in sigmatropic rearrangements: Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487. (p) Nonclassical aryl radicals in sigmatropic rearrangements: Cioslowski, J.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111. (q) Hydrogen [1,5]-shifts in bicyclic systems: Patterson, E. V.; McMahon, R. J. J. Org. Chem. 1997, 62, 4398. (r) Sigmatropic rearrangements in thiophenes, furans, and pyrroles: Tietze, L. F.; Schultz, G. Chem.-Eur. J. 1997, 3, 523. (s) Theoretical study on the hydrogen [1,5]-shift in 1,3-pentadiene: Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 423, 189. (t) [1,5]-Shifts in pyrazole and related systems: Alkorta, I.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1998, 2497. (u) Thermal rearrangements of norcaradiene: Jarzecki, A. A.; Gajewski, J.; Davidson, E. R. J. Am. Chem. Soc. 1999, 121, 6928. (v) The role of geminal bonds in hydrogen [1,5]-shifts: Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166. (w) Hydrogen and chlorine sigmatropic shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625. (x) Oxidation mechanism of D-hydroxyisoprene alkoxy radicals; hydrogen abstraction versus the hydrogen [1,5]-shift: Zhao, J.; Zhang, R. Y.; North, S. W. Chem. Phys. Lett. 2003, 369, 204. (y) Intramolecular aromatic [1,5]-hydrogen transfer in free radical reactions: Karady, S.; Cummins, J. M.; Dannenberg, J. J.; del Rio, E.; Dormer, P. G.; Marcune, B. F.; Reamer, R. A.; Sordo, T. L. Org. Lett. 2003, 5, 1175.
52. (a) [1,5]-Shifts from geminal positions: Rozenberg, V. I.; Nikanorov, V. A.; Ginzburg, B. I.; Reutov, O. A. Bull. Acad. Sci. USSR 1983, 32, 1102.
53. (b) Fluorine effect on kinetics and stereochemistry of sigmatropic rearrangements: Dolbier, W. R.: Alty, A. C.; Phanstiel, O. J. J. Am. Chem. Soc. 1987, 109, 3046.
54. (c) Synthesis of pyrroloquinolines through the irreversible hydrogen [1,5]-shift: Kelderman, E.; Noorlanderbunt, H. G.; Vaneerden, J.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1991, 110, 115.
55. (d) Nonconcerted hydrogen [1,5]-shift in the synthesis of hexahydrojujolidines: Potts, K. T.; Rochanapruk, T.; Padwa, A.; Coats, S. J.; Hadjiarapoglou, L. J. Org. Chem. 1995, 60, 3795.
56. (e) Substituent effects in homodienyl hydrogen [1,5]-shifts in vinylaziridines: Somfai, P.; Ahman, J. Tetrahedron Lett. 1995, 36, 1953.
57. (f) Synthesis of bipyridines through hetero-Diels - Alder reaction and a subsequent hydrogen [1,5]-shift: Brandenburg, J.; Beckert, R.; Fehling, P.; Doring, M.; Gorls, H. J. Prakt. Chem. 1996, 338, 430.
58. (g) Substituent effects in homodienyl hydrogen [1,5]-shifts in vinylaziridines: Ahman, J.; Somfai, P. Tetrahedron 1999, 55, 11595.
59. (h) Biomimetic cascade reactions including a hydrogen [1,5]-shift: Robins, M. J.; Guo, Z. Q.; Samano, M. C.; Wnuk, S. F. J. Am. Chem. Soc. 1999, 121, 1425.
60. (i) Silyl-accelerated [1,5]-hydrogen migrations in vinylcyclopropanes: Lin, Y.-L.; Turos, E. J. Org. Chem. 2001, 66, 8751.
61. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
62. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
63. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
64. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
65. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
66. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
67. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
68. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in transfer of chirality from one end to the other, see: Dehnhardt, C.; McDonald, M.; Lee, S.; Floss, H. G.; Mulzer, J. J. Am. Chem. Soc. 1999, 121, 10848. (b) Thermal isomerization of isovelleral and merulidial: Hansson, T.; Sterner, O.; Wickberg, B.; Bergman, R. J. Org. Chem. 1992, 57, 3822. (c) Biosynthesis of vitamin B12 involving sigmatropic shifts: Scott, A. I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1223. Blanche, F.; Cameron, B.; Crouzet, J.; Debussche, L.; Thibaut, D.; Vuilhorgne, M.; Leeper, F. J.; Battersby, A. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 383. (d) In the synthesis of o-quinodimethanes: Korth, H.-G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. J. Am. Chem. Soc. 1994, 116, 2767. (e) Hydrogen [1,5]- and [1,7]-shifts in bisorthoquinone monoketals: Feldman, K. S. J. Org. Chem. 1997, 62, 4983. (f) Hydrogen [1,5]-shifts in α-sulfonyl-o-quinodimethanes: Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2086. (g) Competition of the hydrogen [1,5]-shift with intramolecular Diels - Alder reaction in the thermolysis of (Z)-1,3,8-nonatriene: Diedrich, M. K.; Klärner, F.-G. J. Am. Chem. Soc. 1998, 120, 6212. (h) Hydrogen [1,5]-shift in synthesis of tetrahydro-7aH-indenes: Wu, H. P.; Aumann, R.; Fröhlich, R.; Wibbeling, B.; Kataeva, O. Chem.-Eur. J. 2001, 7, 5084.
69. A selective but representative summary of synthetic applications of [1,5]-shifts is given in the introduction of ref 8. (a) For a synthesis of "chiral methyl" where the [1,5]-hydrogen shift was the key step in
70. Detailed computational study of hydrogen [1,5]-shifts in pentadienes and heteroanalogues: Saettel, N. J.; Wiest, O. J. Org. Chem. 2000, 65, 2331.
71. Thorough discussion and analysis of the hydrogen [1,5]-shift in 1,3-cyclohexadiene, cycloheptadiene, and cyclooctadiene: Hess, B. A., Jr.; Baldwin, J. E. J. Org. Chem, 2002, 67, 6025.
72. Chlorine and hydrogen [1,7]-and [1,5]-shifts in cycloheptatrienes and cyclopentadienes: Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625.
73. For an authoritative review, see: Transition structures of hydrocarbon pericyclic reactions. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
74. For a highly engaging and personal account of the history of pericyclic reactions, see: Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
75. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
76. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
77. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
78. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
79. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
80. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
81. Note, however, that highly diradicaloid transition states can be involved when the strain required to achieve the continuous bonding in the TS is too large for this allowed process to be favored. [1,5]-Carbon shifts in norcaradienes provide good examples. (a) Theoretical explanation: Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121. 4524. (b) Experimental results: Klärner, F.-G. Top. Stereochem. 1984, 15, 1-42. Klärnerr, F.-G. Angew. Chem., Int Cheni., Int. Ed. Engl. 1974, 13, 268. (c) Klarner, F.-G.; Brassel, B, J. Am. Chem. Soc. 1980, 102, 2469. (d) Klarner, F.-G.; Yaslak, S.; Wette, M. Chem. Ber. 1979, 112, 1168. See also: (e) Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1982, 104, 2857. (f) Baldwin, J. E.; Broline, B. M. J. Org. Chem. 1982, 47, 1385.
82. For an early study on the role of a six-electron transition state in concerted reactions, see: Evans, M. G.; Warhurst, E. Trans. Faraday Soc. 1938, 34, 614. For a review on Hückel-/Möbius-systems, see: Zimmerman, H. Acc. Chem. Res. 1971, 4, 272. For NICS-calculations on aromatic transition states in pericyclic reactions, see: Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.
83. For an early study on the role of a six-electron transition state in concerted reactions, see: Evans, M. G.; Warhurst, E. Trans. Faraday Soc. 1938, 34, 614. For a review on Hückel-/Möbius-systems, see: Zimmerman, H. Acc. Chem. Res. 1971, 4, 272. For NICS-calculations on aromatic transition states in pericyclic reactions, see: Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.
84. For an early study on the role of a six-electron transition state in concerted reactions, see: Evans, M. G.; Warhurst, E. Trans. Faraday Soc. 1938, 34, 614. For a review on Hückel-/Möbius-systems, see: Zimmerman, H. Acc. Chem. Res. 1971, 4, 272. For NICS-calculations on aromatic transition states in pericyclic reactions, see: Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.
85. However, these reactions can be significantly accelerated by the electrostatic field of coordinated metal cations, see: (a) Jiao, H.; Schleyer, P. v. R. J. Chem. Soc., Faraday Trans. 1994, 90, 1559. (b) Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 11529.
86. However, these reactions can be significantly accelerated by the electrostatic field of coordinated metal cations, see: (a) Jiao, H.; Schleyer, P. v. R. J. Chem. Soc., Faraday Trans. 1994, 90, 1559. (b) Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 11529.
87. Lewis, F. D.; Zuo, X.; Gevorgyan, V.; Rubin, M. J. Am. Chem. Soc. 2002, 124, 13664.
88. Similar effects of aromatic stabilization of products on Diels - Alder reactions involving quinodimethides were found by recent theoretical studies: Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 7971. Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 6132. Manoharan, M.; De Proft, F.; Geerlings, P. J. Chem. Soc., Perkin Trans. 2 2000, 1767. Corminboeuf, C.; Heine, T.; Weber, J. Org. Lett. 2003, 5, 1127.
89. Similar effects of aromatic stabilization of products on Diels - Alder reactions involving quinodimethides were found by recent theoretical studies: Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 7971. Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 6132. Manoharan, M.; De Proft, F.; Geerlings, P. J. Chem. Soc., Perkin Trans. 2 2000, 1767. Corminboeuf, C.; Heine, T.; Weber, J. Org. Lett. 2003, 5, 1127.
90. Similar effects of aromatic stabilization of products on Diels - Alder reactions involving quinodimethides were found by recent theoretical studies: Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 7971. Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 6132. Manoharan, M.; De Proft, F.; Geerlings, P. J. Chem. Soc., Perkin Trans. 2 2000, 1767. Corminboeuf, C.; Heine, T.; Weber, J. Org. Lett. 2003, 5, 1127.
91. Similar effects of aromatic stabilization of products on Diels - Alder reactions involving quinodimethides were found by recent theoretical studies: Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 7971. Manoharan, M.; De Proft, F.; Geerlings, P. J. Org. Chem. 2000, 65, 6132. Manoharan, M.; De Proft, F.; Geerlings, P. J. Chem. Soc., Perkin Trans. 2 2000, 1767. Corminboeuf, C.; Heine, T.; Weber, J. Org. Lett. 2003, 5, 1127.
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95. For early reports on the Marcus theory, see: Marcus, R. A. J. Chem. Phys. 1956. 24, 966. Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155. Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
96. For early reports on the Marcus theory, see: Marcus, R. A. J. Chem. Phys. 1956. 24, 966. Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155. Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
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99. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
100. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
101. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
102. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
103. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
104. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
105. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
106. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
107. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
108. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
109. N2 reactions: Wolfe, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694. (d) Electron/proton-transfer reactions and nucleophilic substitutions: Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2660. (e) Aryl-substituted cyclopropylcarbinyl rearrangements: Martinesker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174. (f) Intramolecular reactions; aldol condensations and ester/lactone formation: Guthrie, J. P. Can. J. Chem. 1996, 74, 1283. (g) Intramolecular aldol condensations: Guthrie, J. P.: Guo, J. N. J. Am. Chem. Soc. 1996, 118, 11472. (h) Hydration of carbonyl compounds: Guthrie, J. P. J. Am. Chem. Soc. 2000, 122, 5529. (i) Reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: Canestrari, S.; Marin, A.; Sgarabotto, P.; Righi, L.; Greci, L. J. Chem. Soc., Perkin Trans. 2 2000, 833. (j) [2+3] cycloaddition of ethylene to transition metal complexes: Gisdakis, P.; Rösch, N. J. Am. Chem. Soc. 2001, 123, 697. (k) Electron-transfer dynamics in synthetic DNA hairpins: Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewksi, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
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136. Diamagnetic susceptibility exaltation as a criterion of aromaticity: Dauben, H. J., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811.
137. A comparison of models for calculating nuclear magnetic resonance shielding tensors: Cheeseman, J. R.; Truck, G. W.; Keith, T. A.; Frisch, J. J. Chem. Phys. 1996, 104, 5497.
138. For applications on various rearrangements and pericyclic reactions, including the hydrogen [1,5]-shift, Claisen rearrangement, Cope rearrangement, and 1,3-dipolar cycloadditions, see: (a) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1. (b) Reference 5t.
139. For applications on various rearrangements and pericyclic reactions, including the hydrogen [1,5]-shift, Claisen rearrangement, Cope rearrangement, and 1,3-dipolar cycloadditions, see: (a) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1. (b) Reference 5t.
140. Description of the Bergman-cyclization: (a) Gräfenstein, J.; Hjerpe, A. M.; Kraka, E.; Cremer, D. J. Phys. Chem. A;2000, 104, 1748.
141. (b) Alabugin, I. V.; Manoharan, M.; Kovalenko, S. V. Org. Lett. 2002, 4, 1119.
142. (c) Alabugin, I. V.; Manoharan, M. J. Phys. Chem. A 2003, 107, 3363.
143. Because π-systems of the appended phenyl groups in 2b and 8b are almost orthogonal to the π-systems involved into the pericyclic reaction, the presence of these groups has only a minor (0.3-0.4 kcal/mol) effect on the activation energy.
144. Evaluation of aromatic stabilization energies: Schleyer, P. v. R.; Puhlhofer, F. Org. Lett. 2002, 4, 2873.
145. rxn.
146. (a) These data are in excellent agreement with the aromatic stabilization energies of 19.8 kcal/mol for furan, 22.4 kcal/mol for thiophene, and 25.5 kcal/mol for pyrrole: Schleyer, P. v. R.; Freeman. P. K.; Jiao, H.; Goldfuss, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 337.
147. (b) Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 28, 209.
148. (c) The relative order of aromaticity in five-membered heterocycles has been a matter of extensive discussions which led to revision of some of the earlier assumptions. See, for example: Bernardi, F.; Bottoni, A.; Venturini, A. J. Mol. Struct. (THEOCHEM) 1988, 163, 173 and more than 60 references therein.
149. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity, Wiley: New York, 1994. Garratt, P. J. Aromaticity. Wiley: New York, 1986.
150. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity, Wiley: New York, 1994. Garratt, P. J. Aromaticity. Wiley: New York, 1986.
151. For a recent review, see: Quantitative Measures of Aromaticity for Mono-, Bi-, and Tricyclic Penta- and Hexaatomic Heteroaromatic Ring Systems and Their Interrelationships. Katritzky, A. R.; Jug, K.; Oniciu, D. C. Chem. Rev. 2001, 101, 1421.
152. (a) For particularly well-studied cyclohexadienone/phenol and thione/thiol tautomerizations, see: Beak, P.; Covington, J. B.; White, J. M. J. Org. Chem. 1980, 45, 1347.
153. (b) Tautomerism of 2(1H)-pyridinethione: Nowak, M. J.; Lapinski, L.; Rostkowska, H.; Les, A.; Adamowicz, L. J. Phys. Chem. 1990, 94, 7406. Moran, D.; Sukcharoenphon, K.; Puchta, R.; Schaefer, H. F., III; Schleyer, P. v. R.; Hoff, C. D. J. Org. Chem. 2002, 67, 9061.
154. (b) Tautomerism of 2(1H)-pyridinethione: Nowak, M. J.; Lapinski, L.; Rostkowska, H.; Les, A.; Adamowicz, L. J. Phys. Chem. 1990, 94, 7406. Moran, D.; Sukcharoenphon, K.; Puchta, R.; Schaefer, H. F., III; Schleyer, P. v. R.; Hoff, C. D. J. Org. Chem. 2002, 67, 9061.
155. (c) Formamide and 2-pyridinone: Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645.
156. (d) Heterocyclic disulfides: Stoyanov, S.; Stoyanova, T.; Akrivos, P. D.: Karagiannidis, P.: Nikolov, P. J. Heterocycl. Chem. 1996, 33, 927.
157. (e) 2-Hydroxypyridine/2(1H)-pyridinone system and its thio and seleno analogues: Kwiatkowski, J. S.; Leszczynski, J. L. J. Mol. Struct. 1996, 376, 325.
158. (f) Quantification of aromaticity with an emphasis on heterocycles: Katritzky, A. R.; Jug, K.; Oniciu, D. C. Chem. Rev. 2001, 101, 1421.
159. (g) The [4+2] cycloadditions of conjugated enynes followed by [1,2]-hydrogen shift also lead to aromatization, see: Ananikov, V. J. Phys. Org. Chem. 2001, 14, 109. Prall, M.; Krüger, A.; Schreiner, P. R.; Hopf, H, Chem.-Eur. J. 2001, 7, 4386. Rodríguez, D.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saa, C. J. Phys. Org. Chem. 2003, 68, 1938.
160. (g) The [4+2] cycloadditions of conjugated enynes followed by [1,2]-hydrogen shift also lead to aromatization, see: Ananikov, V. J. Phys. Org. Chem. 2001, 14, 109. Prall, M.; Krüger, A.; Schreiner, P. R.; Hopf, H, Chem.-Eur. J. 2001, 7, 4386. Rodríguez, D.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saa, C. J. Phys. Org. Chem. 2003, 68, 1938.
161. (g) The [4+2] cycloadditions of conjugated enynes followed by [1,2]-hydrogen shift also lead to aromatization, see: Ananikov, V. J. Phys. Org. Chem. 2001, 14, 109. Prall, M.; Krüger, A.; Schreiner, P. R.; Hopf, H, Chem.-Eur. J. 2001, 7, 4386. Rodríguez, D.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saa, C. J. Phys. Org. Chem. 2003, 68, 1938.
162. s symmetry.
163. Leffler, J. E. Science 1953, 117, 340. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
164. Leffler, J. E. Science 1953, 117, 340. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
165. Bell, R. P. Proc. R. Soc. London, Ser. A 1936, 154, 414.
166. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1938, 34, 11.
167. See Table 2S in the Supporting Information for additional information.
168. Effect of tunneling on the kinetics of sigmatropic hydrogen shifts: Grellmann, K.-H.; Schmitt, U.; Weller, H. Chem. Phys. Lett. 1982, 88, 40.
169. Second-order polynomial provides an even better fit between the DFT and Marcus theory (see Figure S3 in the Supporting Information).
170. The correlations between DFT and Marcus activation enthalpies and free energies are equally good.
171. 2 value is exactly 1.
172. When comparing the experimentally observed reaction rates of hydrogen shifts in acyclic and cyclic molecules, one also has to bear in mind the more favorable entropic component of the reaction free energy for the cyclic cases.
173. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed. Wiley: New York, 1998; Vol. 3, p 1792. For more detailed earlier discussions, see: Foster, J. P.; Weinhold, F. F. J. Am. Chem. Soc. 1980, 102, 7211. Reed, A. E.; Weinhold, F. F. J. Chem. Phys. 1983, 78, 4066. Reed, A. E.; Weinstock, F.; Weinhold, F. F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. F. Chem. Rev. 1988, 88, 899.
174. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed. Wiley: New York, 1998; Vol. 3, p 1792. For more detailed earlier discussions, see: Foster, J. P.; Weinhold, F. F. J. Am. Chem. Soc. 1980, 102, 7211. Reed, A. E.; Weinhold, F. F. J. Chem. Phys. 1983, 78, 4066. Reed, A. E.; Weinstock, F.; Weinhold, F. F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. F. Chem. Rev. 1988, 88, 899.
175. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed. Wiley: New York, 1998; Vol. 3, p 1792. For more detailed earlier discussions, see: Foster, J. P.; Weinhold, F. F. J. Am. Chem. Soc. 1980, 102, 7211. Reed, A. E.; Weinhold, F. F. J. Chem. Phys. 1983, 78, 4066. Reed, A. E.; Weinstock, F.; Weinhold, F. F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. F. Chem. Rev. 1988, 88, 899.
176. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed. Wiley: New York, 1998; Vol. 3, p 1792. For more detailed earlier discussions, see: Foster, J. P.; Weinhold, F. F. J. Am. Chem. Soc. 1980, 102, 7211. Reed, A. E.; Weinhold, F. F. J. Chem. Phys. 1983, 78, 4066. Reed, A. E.; Weinstock, F.; Weinhold, F. F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. F. Chem. Rev. 1988, 88, 899.
177. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed. Wiley: New York, 1998; Vol. 3, p 1792. For more detailed earlier discussions, see: Foster, J. P.; Weinhold, F. F. J. Am. Chem. Soc. 1980, 102, 7211. Reed, A. E.; Weinhold, F. F. J. Chem. Phys. 1983, 78, 4066. Reed, A. E.; Weinstock, F.; Weinhold, F. F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. F. Chem. Rev. 1988, 88, 899.
178. The correlation between calculated and Marcus barriers for the 1,5-shifts in all cyclohexadienes and cyclopentadienes studied in this paper is given in the Supporting Information (Figure S4) and is also quite good.
179. The reaction barriers are in a good agreement with the extent of C1 - H bond cleavage and C5⋯H formation at the TS as in the carbocyclic cases. Note, however, that Cl. H⋯C5 angles are very different in the heterocyclic system given in Table 3.
180. This can be associated with the larger lengths of C-Cl bonds which make it easier to maintain continuous overlap with the migrating group in the TS.
181. In theory, the slopes should be equal to 0.5, but in Figure 19 they are close to but not exactly equal to 0.5. In this case, one cannot be sure that this difference is statistically meaningful.
182. Chemical, physical, and optical "hardness" as a function of the HOMO-LUMO gap: Gilman, J. J. Mater. Res. Innovations 1997, 1, 71.
183. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
184. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
185. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
186. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
187. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
188. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
189. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O.
190. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
191. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
192. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
193. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
194. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
195. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
196. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
197. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
198. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
199. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
200. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
201. For a recent review with comprehensive analysis of the HOMO-LUMO gap and absolute and relative hardness in aromatic compounds, see: De Proft, F.; Geerlings, P. Chem. Rev. 2001, 101, 1451. See also: Haddon, R. C.; Fukunaga, T. Tetrahedron Lett. 1980, 21, 1191. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722. Minsky, A.; Meyer, A. Y.; Rabinovitz, M. Tetrahedron 1985, 41, 785. Absolute hardness and relative hardness: Zhou, Z.; Parr, R. G. J. Am. Chem. Soc. 1989, 111, 7371. Chemical hardness and Pauling scale of electronegativity: Komorowski, L. Chem. Phys. 1987, 114, 55. Komorowski, L. In Chemical Hardness (Structure and Bonding, Vol. 80); Sen, K. D., Ed.; Springer-Verlag: Berlin, Heidelberg, 1993; p 45. Polycyclic hydrocarbons: Sinanoglu, O. Int. J. Quantum Chem. Symp. 1988, 22, 143. Sinanoglu, O. Tetrahedron Lett. 1988, 889. Cioslowski, J.; Polansky, O. E. Theor. Chim. Acta 1988, 74, 55. Kekulene and antikekulene: Babic, D.; Trinajstic, N. J. Mol. Struct. (THEOCHEM) 1994, 120, 321. "Superbenzene": Cioslowski, J.; O'Conner, P. B.; Fleischmann, E. D. J. Am. Chem. Soc. 1991, 113, 1086. Nonbenzenoid polycyclic aromatics: Bird, C. W. Tetrahedron 1998, 54, 10179 and references therein. Five-membered heteroaromatic compounds. Bean, G. J. Org. Chem. 1998, 63, 2497. Aromatic carbonyl compounds: Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503. Derivatives of molecular valence as a measure of aromaticity. Balawender, R.; Komorowski, L.; De Proft, F.; Geerlings, P. J. Phys. Chem. A 1998, 102, 9912. Magnetic properties of large polybenzenoid hydrocarbons. Moran, D.; Stahl, F.; Bettinger, H. F.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746. The influence of the topology on the HOMO-LUMO energy gap in polyacenes. Andre, J.-M.; Champagne, B.; Perpete, E. A.: Guillaume, M. Int. J. Quantum Chem. 2001, 84, 607.
202. For a recent example of engineering the HOMO-LUMO gap in control of redox behavior, electron transfer, and spectroscopic properties, see: Perepichka, D. F.; Bryce, M. R.; Batsanov, A. S.; McInnes, E. J. L.; Zhao, J. P.; Farley, R. D. Chem.-Eur. J. 2002, 8, 4656.
203. Nonlinear optical properties and the HOMO-LUMO gap of polyacenes. Lu, Y.-J.; Lee, S.-L. Chem. Phys. 1994, 179, 431.
204. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
205. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
206. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
207. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
208. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
209. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
210. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
211. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
212. Effect of the HOMO-LUMO gap on conductance of organic molecules: Joachim, C.; Vinuesa, J. F. Europhys. Lett. 1996, 33, 635. Roitberg, A.; Mujica, V.; Ratner, M. A. 215th ACS National Meeting, Dallas, March 29-April 2, 1998. Kato, T.; Yamabe, T. J. Chem. Phys. 2003, 118, 3804. Yamaguchi, Y. J. Chem. Phys. 2003, 117, 9688. Kubiak, C. P.; Kasibhatla, B. S. T. 221st ANYL-180. Abstracts of Papers - American Chemical Society, 2001. Effect of location of the HOMO and LUMO levels with respect to the Fermi level of the metal electrode on conducting properties of molecular wires: Bredas, J. L.: Geskin, V. M.; dos Santos, D. A.; Beljonne, D.; Cornil, J. Appl. Sci. 1997, 341, 47. HOMO-LUMO gap as a structural element in the design of molecular metals. Kobayashi, A.; Suzuki, W.; Fujiwara, E.; Tanaka, H.; Okano, Y.; Kobayashi, H. Synth. Met. 2003, 133-134, 393. Kobayashi, A.; Tanaka, H.; Kobayashi, H. J. Mater. Chem. 2001, 11, 2078. For an example of a practical application in design of conducting copolymers, see: Wang, F.; Lai, Y.-H. Macromolecules 2003, 36, 536.
213. (a) Pentacenes: Cornil, J.; Calbert, J. Ph.; Bredas, J. L. J. Am. Chem. Soc. 2001, 123, 1250. Lin, Y.-Y.; Gundlach, D. J.; Nelson, S.; Jackson T. N. IEEE Trans. Electron Devices 1997, 44, 1325. Herwig, P. T.; Müllen, K. Adv. Mater. 1999, 11, 480. Functionalized pentacenes: Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
214. (a) Pentacenes: Cornil, J.; Calbert, J. Ph.; Bredas, J. L. J. Am. Chem. Soc. 2001, 123, 1250. Lin, Y.-Y.; Gundlach, D. J.; Nelson, S.; Jackson T. N. IEEE Trans. Electron Devices 1997, 44, 1325. Herwig, P. T.; Müllen, K. Adv. Mater. 1999, 11, 480. Functionalized pentacenes: Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
215. (a) Pentacenes: Cornil, J.; Calbert, J. Ph.; Bredas, J. L. J. Am. Chem. Soc. 2001, 123, 1250. Lin, Y.-Y.; Gundlach, D. J.; Nelson, S.; Jackson T. N. IEEE Trans. Electron Devices 1997, 44, 1325. Herwig, P. T.; Müllen, K. Adv. Mater. 1999, 11, 480. Functionalized pentacenes: Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
216. (a) Pentacenes: Cornil, J.; Calbert, J. Ph.; Bredas, J. L. J. Am. Chem. Soc. 2001, 123, 1250. Lin, Y.-Y.; Gundlach, D. J.; Nelson, S.; Jackson T. N. IEEE Trans. Electron Devices 1997, 44, 1325. Herwig, P. T.; Müllen, K. Adv. Mater. 1999, 11, 480. Functionalized pentacenes: Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
217. (b) Linear monodisperse π-conjugated oligomers: Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 8, 1351.