Revisiting hydrogen [1,5] shifts in cyclopentadiene and cycloheptatriene as bimolecular reactions

Journal of Chemical Theory and Computation

Volumn 1, Issue 5, 2005, Pages 944-952

  Yamabe, Shinichi ^a   Tsuchida, Noriko ^a   Yamazaki, Shoko ^a  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750347032     PISSN: 15499618     EISSN: 15499626     Source Type: Journal    
DOI: 10.1021/ct0500646     Document Type: Article

References (41)

1. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: New York, 1970.
2. (a) Fukui, K. Theory of Orientation and Stereoselection; Springer: New York, 1970.
3. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: New York, 1976.
4. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
5. Spangler, C. W. Chem. Rev. 1976, 76, 187.
6. (a) Dormans, G. J. M.; Buck, H. M. J. Mol. Struct. 1986, 136, 121.
7. (b) Dormans, G. J. M.; Buck, H. M. J. Am. Chem. Soc. 1986, 108, 3253.
8. (c) Hess, B. A., Jr.; Schaad, L. J.; Pancir, J. J. Am. Chem. Soc. 1985, 107, 149.
9. (d) Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1983, 105, 7185.
10. (e) Dewar, M. J. S.; Merz, J. M.; Stewart, J. J. P. J. Chem. Soc. Chem. Commun. 1985, 166.
11. (f) Castenmiller, W. A. M.; Buck, H. M. Tetrahedron 1979, 35, 397.
12. (g) Jensen, F. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139.
13. (h) Dewar, M. J. S.; Healr, E. F.; Merz, J. M. J. Am. Chem. Soc. 1988, 110, 2666.
14. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98.
15. (a) Wassermann, A. Diels-Alder Reactions; Elsevier: London, 1965.
16. (b) Sangwan, N. K.; Schneider, H.-J. J. Chem. Soc, Perkin Trans. 2. 1989, 1223.
17. (c) Jorgensen, W. L.; Blake, J. F.; Lim, D.; Severance, D. L. J. Chem. Soc. Faraday Trans. 1994, 90, 1727.
18. (d) Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923.
19. Alder, K.; Ache, H. J. Chem. Ber. 1962, 95, 503;511.
20. (a) Kahn, S. D.; Hehre, W. J.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 8291.
21. (b) Rondan, N. G.; Houk, K. N. Tetrahedron Lett. 1984, 25, 2519.
22. (c) Bachrach, S. M. J. Org. Chem. 1993, 58, 5414.
23. (d) Okajima, T.; Imafuku, K. J. Org. Chem. 2002, 67, 625.
24. (a) Caramella, P.; Quadrelli, P.; Toma, L. J. Am. Chem. Soc. 2002, 124, 1130.
25. (b) Jamróz, M.; Galka, S.; Dobrowolski, J. C. THEOCHEM 2003, 634, 225.
26. Roth, W. R. Tetrahedron Lett. 1964, 1009.
27. Roth, W. R.; Konig, J. Justus Liebigs Ann. Chem. 1966, 699, 24.
28. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11.1; Gaussian, Inc.: Pittsburgh, PA, 2001.
31. Onsager, L. J. Am. Chem. Soc. 1938, 58, 1486.
32. The geometries of CPD-IVb, CPD-IIIb, CPD-VIIb, and CPD-VIIIb were made by changing all the signs of the Cartesian coordinates of the geometries of CPD-IVa, CPD-IIIa, CPD-VIIa, and CPD-VIIIa. The energies of CPD-IVb, CPD-IIIb, CPD-VIIb, and CPD-VIIIb are the same as those of CPD-IVa, CPD-IIIa, CPD-VIIa, and CPD-VIIIa.
33. Wigner, E. P. Phys. Chem. 1933, B19, 203.
34. McLean, S.; Webster, C. J.; Rutherford, R. J. D. Can. J. Chem. 1969, 47, 1555.
35. (a) Ter Borg, A. P.; Razenberg, E.; Kloosterziel, H. Recl. Trav. Chim. Pays-Bas 1965, 84, 1230.
36. (b) Egger, K. W. J. Am. Chem. Soc. 1967, 89, 3688.
37. (a) Cookson, R. C.; Drake, B. V.; Hudec, J.; Morrison, A. J. Chem. Soc, Chem. Commun. 1966, 15.
38. (b) Ito, S.; Fujise, Y.; Okuda, T.; Inoue, Y. Bull. Chem. Soc. Jpn. 1966, 39, 1351.
39. CHT has a geometric isomer, bicyclo[4.1.0]hepta-2, 4-diene (norcaradiene, NCD). NCD has a puckered conformation, which is apparently suitable for the intramolecular hydrogen shift. However, NCD cannot be a reactant for the hydrogen shift, because the cyclopropyl ring in NCD precludes the hydrogen-bridged TS structure. Cycloadditions between CHT and NCD were calculated and are less stable than the ratedetermining step VIIa, b in Figure 8. A series of isomerizations of methyl-NCDs were observed. They would involve intermediates of cycloadducts of two methyl-CHTs.
40. (a) Berson, J. A.; Willcot, M. R., III; J. Am. Chem. Soc. 1965, 87, 2751.
41. (b) Berson, J. A.; Willcot, M. R., III; J. Am. Chem. Soc. 1965, 87, 2752.