A Model Study of the Mechanism of the Type B (Di-π-methane) and Lumiketone Rearrangement in Rotationally Constrained α,β-Enones

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6897-6902

  Reguero, Mar ^a   Bernardi, Fernando ^c   Olivucci, Massimo ^c   Robb, Michael A ^b  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b KING'S COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000945069     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961204u     Document Type: Article

References (42)

1. (a) Zimmerman, H. E. Adv. Photochem. 1963, 1, 183-208.
2. (b) Zimmerman, H. E. Acc. Chem. Res. 1982, 10, 312-317.
3. (c) Zimmerman J. Am. Chem. Soc. 1966, 88, 1566-1567.
4. Zimmerman, H. E., Epling, G. A. J. Am. Chem. Soc. 1972, 94, 8749-8761.
5. (e) Zimmerman, H. E. Acc. Chem. Res. 1972, 5, 393-401.
6. (f) Zimmerman, H. E.; Factor R. E. J. Am. Chem. Soc. 1980, 102, 3538-3548.
7. (g) Zimmerman H. E. Topics Curr. Chem. 1982, 100, 45-73.
8. Reviews on the subject: (a) Schuster, D. I. In Rearrangements in Ground and Excited States; de Mayo P., Ed.; Academic Press: London, 1980; Vol. 3, pp 167-279. (b) Schuster, D. I. In The Chemistry of Enones; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: Chichester, U.K., 1989, Vol. 2, pp 623-756.
9. Reviews on the subject: (a) Schuster, D. I. In Rearrangements in Ground and Excited States; de Mayo P., Ed.; Academic Press: London, 1980; Vol. 3, pp 167-279. (b) Schuster, D. I. In The Chemistry of Enones; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: Chichester, U.K., 1989, Vol. 2, pp 623-756.
10. (a) Zimmerman, H. E.; Kutateladze, A. G.; Maekawa, Y.; Mangette, J. E. J. Am. Chem. Soc. 1994, 116, 9795-9796.
11. (b) Zimmerman, H. E.; Kutateladze, A. G. J. Org. Chem. 1995, 60, 6008-6009.
12. (a) Zimmerman, H. E.; Hahn, R. C.; Morrison, H.; Wani, M. C. J. Am. Chem. Soc. 1965, 87, 1138-1140.
13. (b) Zimmerman, H. E.; Sam, D. J. J. Am. Chem. Soc. 1966, 88, 4905-4914.
14. (c) Zimmerman, H. E.; Rieke, R. D.; Scheffer, J. R. J. Am. Chem. Soc. 1967, 89, 2033-2047.
15. (d) Zimmerman, H. E.; Morse, R. L. J. Am. Chem. Soc. 1968, 90, 954-966.
16. (e) Zimmerman, H. E.; King, R. K.; Xu, J. H.; Caufield, C. E. J. Am. Chem. Soc. 1985, 107, 7724-7732.
17. (f) Zimmerman, H. E.; Lamers, P. H. J. Org. Chem. 1989, 54, 5788-5804.
18. Zimmerman, H. E.; Weber, R. W. J. Am. Chem. Soc. 1989, 111, 995-1007.
19. Dauben, W. G.; Spitzer, W. A.; Kellogg, M. S. J. Am. Chem. Soc. 1971, 93, 3674-3677.
20. Blok, P. M. L.; Jacobs, H. J. C.; Dekkers, H. P. J. M. J. Am. Chem. Soc. 1991, 113, 794-801.
21. Bonneau, R. J. Am. Chem. Soc. 1980, 102, 3816-3822.
22. Schuster, D. I.; Brown, R. H.; Resnick, B. M. J. Am., Chem. Soc. 1978, 100, 4504-4512.
23. Chan, A. C.; Schuster, D. I. J. Am. Chem. Soc. 1986, 108, 4561-4567.
24. Schuster, D. I.; Dunn, D. A.; Heibel, G. E.; Brown, P. B.; Rao, J. M.; Woning, J.; Bonneau, R. J. Am. Chem. Soc. 1991, 113, 6245-6255.
25. Chan, C. B.; Schuster, D. I. J. Am. Chem. Soc. 1982, 104, 2928-2929.
26. Bunce, R. A.; Taylor, V. L.; Holt, E. M. J. Photochem. Photobiol. A: Chem 1992, 68, 263-277.
27. Zimmerman H. E.; Wilson J. W. J. Am. Chem. Soc. 1964, 86, 4036-4042.
28. Zimmerman, H. E.; Lewis, R. G.; McCullough, J. J.; Padwa, A.; Staley, S.; Semmelhack, M. J. Am. Chem. Soc. 1966, 88, 159-161.
29. (b) Zimmerman, H. E.; Sam, D. J J. Am. Chem. Soc. 1966, 88, 4114-4116.
30. (c) Zimmerman, H. E.; Solomon, R. D. J. Am. Chem. Soc. 1986, 108, 6276-6289.
31. Chapman, O. L.; Clardy, J. C.; McCowell, T. L.; Wright H. E. J. Am. Chem. Soc. 1973, 95, 5086-5087.
32. Schuster, D. I.; Lem. G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22.
33. Yamanuchi, S.; Hirota, N.; Higuchi,J. J. Phys. Chem. 1988, 92, 2129-2133.
34. Schuster, D. I.; Woning, J.; Kaprinidis, N. A.; Pan, Y.; Cai, B.; Barra, M.; Rhodes, C. A. J. Am. Chem. Soc. 1992, 114, 7029-7034.
35. Kaprinidis, N. A.; Lem, G.; Courtney S. H.; Schuster, D. I. J. Am. Chem. Soc. 1993, 115, 3324-3325.
36. Reguero, M.; Olivucci, M.; Bernardi, F.; Robb, M. A. J. Am. Chem. Soc. 1991, 116, 2103-2114.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B; Gaussian, Inc.: Pittsburgh PA, 1994.
38. (a) Ragazos, I. N.; Robb, M. A.; Bernardi, F.; Qlivucci, M. Chem. Phys. Lett 1992, 197, 217.
39. (b) Bearpark, M. J.; Robb, M. A.; Schlegel, H. B. Chem. Phys. Lett. 1994 223, 269.
40. Koseki, S.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. 1992, 96, 10768.
41. Zimmerman, H. E. Tetrahedron 1974, 30, 1617-1628.
42. Schuster, D. I.; Heibel, G. E.; Woning, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1345-1347.