Density functional study of some germylene insertion reactions

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4229-4237

  Su, Ming Der ^a   Chu, San Yan ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; METHANE;

ARTICLE; ATOMIC PARTICLE; CHEMICAL REACTION; GEOMETRY; MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033526388     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983763j     Document Type: Article

References (65)

1. Lange, L.; Meyer, B.; DuMont, W.-W. J. Organomet. Chem. 1987, 329, C17.
2. Neumann, W. P. Chem. Rev. 1991, 91, 311.
3. (a) Lukevics, E.; Gar, T.; Ignatovich, L.; Mironov, B. In Biological Activity of Germanium, Zinatne, Riga: 1990.
4. (b) Lukevics, E.; Ignatovich, L. In Frontiers of Organogermanium-Tin-Lead Chemistry; Latvian Institute: Riga, 1993.
5. (c) Patai, S. In the Chemistry of Organic Germanium, Tin and Lead Compounds; Wiley: New York, 1995.
6. Motooka, T.; Greene, J. E. J. Appl. Phys. 1986, 59, 2015.
7. Du, W.; Keeling, L. A.; Greenlief, C. M. J. Vac. Sci. Technol. 1994, A12, 2281.
8. Isobe, C.; Cho, H.; Crowell, J. E. Surf. Sci. 1993, 295, 117.
9. Lu, G.; Crowell, J. E. J. Chem. Phys. 1993, 98, 3415.
10. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
11. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
12. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
13. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
14. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
15. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) oss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
16. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
17. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
18. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
19. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
20. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
21. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
22. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
23. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
24. For reviews, see: (a) Hine, J. In Divalent Carbon; Academic Press: New York, 1964. (b) Krimes, W. In Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1. (c) Bethell, D. Adv. Phys. Org. Chem. 1969, 7, 153-209. (d) Moss, R. A. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88. (e) Krimes, W. In Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8. (f) Moss, R. A.; Jones, M., Jr. In Carbenes; Wiley: New York, 1973; Vol. 1. (g) Jones, M., Jr.; Moss, R. A. In Carbenes; Wiley: New York, 1975; Vol. 2. (h) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (i) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3. (j) Moss, R. A.; Jones, M., Jr. In Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3. (k) Abramovitch, R. A. In Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (l) Platz, M. S. In Kinetics And Spectroscope of Carbenes And Biradicals; Plenum: New York, 1990. (m) DeMore, W. B.; Benson, S. W. Adv. Photochem. 1964, 2, 219-261. (n) Tomioka, H. Res. Chem. Intermed. 1994, 20, 605-634. (o) Closs, G. L. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Interscience: New York, 1968; Vol. 3, pp 193-235.
25. Jutzi, P.; Schmidt, H.; Neumann, B.; Stammler, H.-G. Organometallics 1996, 15, 741.
26. Lei, D.; Lee, M. E.; Gaspar, P. P. Tetrahedron 1997, 53, 10179.
27. Karolczak, J.; Harper, W. W.; Grev, R. S.; Clouthier, D. J. J. Chem. Phys. 1995, 103, 2839.
28. Bunker, P. R.; Phillips, R. A.; Buenker, R. J. Chem. Phys. Lett. 1984, 110, 351.
29. Phillips, R. A.; Buenker, R. J.; Beardsworth, R.; Bunker, P. R.; Jensen, P.; Kraemer, W. P. Chem. Phys. Lett. 1985, 118, 60.
30. Isabel, R. J.; Guillory, W. A. J. Chem. Phys. 1972, 57, 1116.
31. Smith, G.; Guillory, W. A. J. Chem. Phys. 1972, 56, 1423.
32. Harper, W. W.; Ferrall, E. A.; Hilliard, R. K.; Stogner, S. M.; Grev, R. S.; Clouthier, D. J. J. Am. Chem. Soc. 1997, 119, 8361.
33. Takeo, H.; Curl, R. F.; Wilson, P. W. J. Mol. Spectrosc. 1971, 38, 464.
34. Karolczak, J.; Grev, R. S.; Clouthier, D. J. J. Chem. Phys. 1994, 101, 891.
35. Haruhiko, I.; Hirota, E.; Kuchitsu, K. Chem. Phys. Lett. 1990, 175, 384.
36. Harper, W. W.; Clouthier, D. J. J. Chem. Phys. 1998, 108, 416.
37. Hastie, J. W.; Hauge, R. H.; Margrave, J. L. J. Mol. Spectrosc. 1969, 29, 152.
38. Karolczak, J.; Zhuo, Q.; Clouthier, D. J.; Davis, W. M.; Goddard, J. D. J. Chem. Phys. 1993, 98, 60.
39. Haruhiko, I.; Hirota, E.; Kuchitsu, K. Chem. Phys. Lett. 1991, 177, 235.
40. Coffin, J. M.; Hamilton, T. P.; Pulay, P.; Hargittai, I. Inorg. Chem. 1989, 28, 4092.
41. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
42. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
43. Becke, A. D. J. Chem. Phys. 1993, 93, 5648.
44. Su, M.-D.; Chu, S.-Y. Submitted.
45. (a) For carbon, see: Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. (b) For germanium, see: Curtiss, L. A.; McGrath, M. P.; Blaudeau, J.-P.; Davis, N. E.; Binning, R. C.; Radom, L. J. Chem. Phys. 1995, 103, 6104.
46. (a) For carbon, see: Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. (b) For germanium, see: Curtiss, L. A.; McGrath, M. P.; Blaudeau, J.-P.; Davis, N. E.; Binning, R. C.; Radom, L. J. Chem. Phys. 1995, 103, 6104.
47. Frisch, M. J.; Polpe, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
48. Gaussian 94: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople. Gaussian, Inc., Pittsburgh, PA, 1995.
49. 2v, symmetry throughout this work, even the molecule has no symmetry at all.
50. Albright, T. A.; Burdett, J. K.; Whangbo, M.-H. In Orbital interactions in Chemistry; John Wiley & Sons: New York, 1985.
51. Harrison, J. F.; Liedtke, R. C.; Liebman, J. F. J. Am. Chem. Soc. 1979, 101, 7162.
52. 2.
53. Hammond, G. S. J. Am. Chem. Soc. 1954, 77, 334.
54. Bach, R. D.; Su, M.-D.; Aldabagh, E.; Andres, J. L.; Schlegel, H. B. J. Am. Chem. Soc. 1993, 115, 10237.
55. (a) Sawrey, B. A.; O'Neal, H. E.; Ring, M. A.; Coffey, D. Int. J. Chem. Kinet. 1984, 16, 31.
56. (b) Davidson, I. M. T.; Lawrence, F. T.; Ostah, N. A. J. Chem. Soc., Chem. Commun. 1980, 659.
57. However, the general trend of the B3LYP method to underestimate barrier heights is well-known, and it suggests that this B3LYP value is a lower limit.
58. (a) Shaik, S.; Schlegel, H. B.; Wolfe, S. In Theoretical Aspects of Physical Organic Chemistry; John Wiley & Sons Inc.: New York, 1992.
59. (b) Pross, A. In Theoretical and Physical principles of Organic Reactivity; John Wiley & Sons Inc.: New York, 1995.
60. Su, M.-D. Inorg. Chem. 1995, 34, 3829.
61. See ref 32, pp 116.
62. Siegbahn, P. E. M. J. Am. Chem. Soc. 1996, 118, 1487.
63. Irikura, K. K.; Goddard, W. A., III; Beauchamp, J. L. J. Am. Chem. Soc. 1992, 114, 48.
64. Such π-back-bonding is commonplace in transition metal chemistry, although the ligands are usually the σ-donore and π-acceptors in that context.
65. Su, M.-D.; Chu, S.-Y. Submitted.