Electron-Transfer Reactions of Aromatic α,βEpoxy Ketones: Factors That Govern Selective Conversion to β-Diketones and β-Hydroxy Ketones

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2396-2400

  Hasegawa, Eietsu ^a   Ishiyama, Kenyuki ^a   Fujita, Takayuki ^a   Kato, Tomoyasu ^a   Abe, Toshiaki ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000881634     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622439     Document Type: Article

References (52)

1. (a) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399,
2. (b) Pradhan, S. K. Tetrahedron 1986, 42, 6351.
3. (c) Eberson, L. Electron Transfer Reactions in Organic Chemistry: Springer-Verlag: Berlin, 1987.
4. (d) Photoinduced Electron Transfer, Part C; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988.
5. (a) Hasegawa, E.; Ishiyama, K.; Horaguchi, T.; Shimizu, T. J. Org. Chem. 1991, 56, 1631.
6. (b) On the contrary, Cossy and co-workers reported that β-hydroxy ketone was a major isolable product in the photoreaction of chalcone epoxide 1a with triethylamine: Cossy, J.; Bouzide, A.; Ibhi, S.; Aclinou, P. Tetrahedron 1991, 47, 7775.
7. Yoon, U. C.; Mariano, P. S.; Givens, R. S.; Atwater, B. W., III. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, 1994; Vol. 4; pp 117-205.
8. 4b
9. (b) Pandey, B.; Dalvi, P. V.; Athawale, A. A.; Pant, B. G.; Kewale, P. P. J. Chem. Soc., Chem. Commun. 1990, 1505.
10. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596.
11. 6b
12. (b) Kumar, C. V.; Ramaiah, D.; Das, P. K.; George, M. V. J. Org. Chem. 1985, 50, 2818:
13. 7b
14. (b) Hasegawa, E.; Ishiyama, K.; Horaguchi, T.; Shimizu, T. Tetrahedron Lett. 1991, 32, 2029.
15. 8c
16. 4.
17. (c) Wagner, P. J.; Truman, R. J.; Puchalski, A. E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727.
18. 1H NMR analyses of the reaction mixtures suggested that the peaks for 2b and 3b observed for the reactions in acetonitrile were significantly smaller than those in benzene. The isolated yields of 2b and 3b were indeed low in such cases (compare entries 1 and 5 with 2 and 6 in Table 2, respectively). Therefore, the relatively low yields in Table 2 would not be mainly due to the isolation technique although it was, of course, difficult to isolate the low-yielding products, particularly at the low conversion of 1b in acetonitrile. The formation of benzaldehyde was sometimes observed in the crude reaction mixture; however, its yield (not determined) appeared to be low. Eventually, we were unable to isolate and identify the other products from the photoreaction mixture.
19. 10b
20. (b) Zhang, X.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211.
21. Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev, 1978, 78, 243.
22. (a) See ref 11.
23. (b) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337.
24. 13b
25. (b) Devadoss, C.; Fessenden, R. W. J. Phys. Chem. 1990, 94, 4540; 1991, 95, 7253.
26. (b) Devadoss, C.; Fessenden, R. W. J. Phys. Chem. 1990, 94, 4540; 1991, 95, 7253.
27. 14b
28. (b) Liu, W. Z.; Bordwell, F. G. J. Org. Chem. 1996, 61, 4778.
29. 15b,c,d
30. (b) Simon, J. D.; Peters, K. S. J. Am. Chem. Soc. 1983, 105, 4875.
31. (c) Hasegawa, E.; Xu, W.; Mariano, P. S.; Yoon, U. C.; Kim, J. U. J. Am. Chem. Soc. 1988, 110, 8099.
32. (d) Salt effects on organic reactions in general: Loupy, A.; Tchoubar, B.; Astruc, D. Chem. Rev. 1992, 92, 1141.
33. 16b
34. (b) Hasegawa, E.; Kato, T.; Kitazume, T.; Yanagi, K.; Hasegawa, K.; Horaguchi, T. Tetrahedron Lett. 1996, 48, 7079.
35. (a) Robinson, C. H.; Henderson, R. J. Org. Chem. 1972, 37, 565.
36. (b) Weile, G. R.; McMorris, T. C. J. Org. Chem. 1978, 43, 3942.
37. (c) Shapiro, E. L.; Gentles, M. J.; Kabasakalian, P.; Magatti, A. J. Org. Chem. 1981, 46, 5017.
38. (d) Osuka, A.; Takaoka, K.; Suzuki, H. Chem. Lett. 1984, 271.
39. (e) McChesney, J. D.; Thompson, T. N. J. Org. Chem. 1985, 50, 3473.
40. (f) Miyashita, M.; Suzuki, T.; Yoshikoshi, A. Tetrahedron Lett. 1987, 28, 4293.
41. (g) Inokuchi, T.; Kusumoto, M.; Torii, S. J. Org. Chem. 1990, 55, 1548.
42. (h) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T.; Tanaka, S.; Yamashita, Y. J. Org. Chem. 1992, 57, 5352.
43. (i) Engman, L.; Stern, D. J. Org. Chem. 1994, 59, 5179.
44. (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307 and references cited therein.
45. (b) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
46. 19b
47. (b) Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 55, 5008.
48. Addition of triethylamine (5 equiv) indeed reduced the yield of enone to less than 10%, which seems to be consistent with this consideration. However, the fact that the yield of 3a became low (about 20%) was also witnessed, a result that is not easy to rationalize.
49. Hasegawa, E.; Brumfield, M. A.; Mariano, P. S.; Yoon, U. C. J. Org. Chem. 1988, 53, 5435.
50. Benington, F.; Morin, R. D.; Clark, L. C. J. Org. Chem. 1955, 20, 102.
51. Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821.
52. Imamoto, T.; Ono, M. Chem. Lett. 1987, 501.