Exploratory studies of H-atom abstraction and silyl-transfer photoreactions of silylalkyl ketones and (silylalkyl)phthalimides

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3304-3314

  Lee, Yean Jang ^a   Ling, Rong ^a   Mariano, Patrick S ^a   Yoon, Ung Chan ^b   Kim, Dong Uk ^b   Oh, Sun Wha ^b  

^a Bldg 142   (United States)

^b Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000566633     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522623     Document Type: Article

References (36)

1. Wagner, P. J. Top. Curr. Chem. 1976, 66. 1. Wagner, P. J. Rearrangements in Ground and Excited States; deMayo, P., Ed., Academic Press: New York, 1980; Vols 42 and 43. Wagner, P. J.; Park, B -S. Organic Photochemistry; Padwa A., Ed ; Marcel Dekker,: New York, 1991; Vol. 11.
2. Wagner, P. J. Top. Curr. Chem. 1976, 66. 1. Wagner, P. J. Rearrangements in Ground and Excited States; deMayo, P., Ed., Academic Press: New York, 1980; Vols 42 and 43. Wagner, P. J.; Park, B -S. Organic Photochemistry; Padwa A., Ed ; Marcel Dekker,: New York, 1991; Vol. 11.
3. Wagner, P. J. Top. Curr. Chem. 1976, 66. 1. Wagner, P. J. Rearrangements in Ground and Excited States; deMayo, P., Ed., Academic Press: New York, 1980; Vols 42 and 43. Wagner, P. J.; Park, B -S. Organic Photochemistry; Padwa A., Ed ; Marcel Dekker,: New York, 1991; Vol. 11.
4. Yang, N. C.; Morduchowitz, A.; Yang, D-D. H. J. Am. Chem. Soc. 1963, 85, 1017.
5. Scheffer, J. R.; Garcia-Garibay, M.; Nalamasu, O. Organic Photochemistry, Padwa, A., Ed.; Marcel Dekker: New York, 1987; Vol. 8.
6. Wagner, P. S. Acc Chem. Res. 1983, 16, 461.
7. Kanaoka, Y.; Migita, Y., Sato, Y.; Nakai, H. Heterocycles, 1974, 2, 621. Sato, Y ; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y., Hatanaka, Y.; Kanaoka, Y Chem. Pharm. Bull. 1982, 30, 1639 Sato, Y.; Nakai, H.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Kanaoka, Y. Tetrahedron Lett 1973, 4565. Kanaoka, Y.; Nagasawa, C., Nakai, H., Sato, Y., Ogiwara, H.; Mizoguchi, T. Heterocycles 1975, 3, 553.
8. Kanaoka, Y.; Migita, Y., Sato, Y.; Nakai, H. Heterocycles, 1974, 2, 621. Sato, Y ; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y., Hatanaka, Y.; Kanaoka, Y Chem. Pharm. Bull. 1982, 30, 1639 Sato, Y.; Nakai, H.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Kanaoka, Y. Tetrahedron Lett 1973, 4565. Kanaoka, Y.; Nagasawa, C., Nakai, H., Sato, Y., Ogiwara, H.; Mizoguchi, T. Heterocycles 1975, 3, 553.
9. Kanaoka, Y.; Migita, Y., Sato, Y.; Nakai, H. Heterocycles, 1974, 2, 621. Sato, Y ; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y., Hatanaka, Y.; Kanaoka, Y Chem. Pharm. Bull. 1982, 30, 1639 Sato, Y.; Nakai, H.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Kanaoka, Y. Tetrahedron Lett 1973, 4565. Kanaoka, Y.; Nagasawa, C., Nakai, H., Sato, Y., Ogiwara, H.; Mizoguchi, T. Heterocycles 1975, 3, 553.
10. Kanaoka, Y.; Migita, Y., Sato, Y.; Nakai, H. Heterocycles, 1974, 2, 621. Sato, Y ; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y., Hatanaka, Y.; Kanaoka, Y Chem. Pharm. Bull. 1982, 30, 1639 Sato, Y.; Nakai, H.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Kanaoka, Y. Tetrahedron Lett 1973, 4565. Kanaoka, Y.; Nagasawa, C., Nakai, H., Sato, Y., Ogiwara, H.; Mizoguchi, T. Heterocycles 1975, 3, 553.
11. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233. Mariano, P S. Acc. Chem. Res. 1983, 16, 130, Zhang, X.-M.; Yeh, S.-R ; Hong, S.; Freecaro, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am Chem. Soc. 1994, 116, 4211. d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
12. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233. Mariano, P S. Acc. Chem. Res. 1983, 16, 130, Zhang, X.-M.; Yeh, S.-R ; Hong, S.; Freecaro, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am Chem. Soc. 1994, 116, 4211. d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
13. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233. Mariano, P S. Acc. Chem. Res. 1983, 16, 130, Zhang, X.-M.; Yeh, S.-R ; Hong, S.; Freecaro, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am Chem. Soc. 1994, 116, 4211. d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
14. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233. Mariano, P S. Acc. Chem. Res. 1983, 16, 130, Zhang, X.-M.; Yeh, S.-R ; Hong, S.; Freecaro, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am Chem. Soc. 1994, 116, 4211. d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
15. Ahmed-Schofield, R.; Mariano, P. S. J. Og. Chem. 1987, 52, 1478. Ho, G. D.; Mariano, P S. J. Org. Chem. 1988, 53, 5113. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611.
16. Ahmed-Schofield, R.; Mariano, P. S. J. Og. Chem. 1987, 52, 1478. Ho, G. D.; Mariano, P S. J. Org. Chem. 1988, 53, 5113. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611.
17. Ahmed-Schofield, R.; Mariano, P. S. J. Og. Chem. 1987, 52, 1478. Ho, G. D.; Mariano, P S. J. Org. Chem. 1988, 53, 5113. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611.
18. Yoon, U. C.; Kim, D. U.; Woo, C. W.; Choi, Y. S.; Lee, Y. L.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698 Yoon, U. C.; Cho, S. J.; Lee, Y. J.; Mancheno, J. M.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353.
19. Yoon, U. C.; Kim, D. U.; Woo, C. W.; Choi, Y. S.; Lee, Y. L.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698 Yoon, U. C.; Cho, S. J.; Lee, Y. J.; Mancheno, J. M.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353.
20. Clovin, E. Silicon in Organic Synthesis; Butterworth: London, 1981; Chapter 2.
21. Alberti, A.; Dellonte, S.; Paradisi, C ; Roffia, S.; Pedulli, G. F. J. Am Chem. Soc: 1990, 112, 1123. Sakamoto, K.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1466.
22. Alberti, A.; Dellonte, S.; Paradisi, C ; Roffia, S.; Pedulli, G. F. J. Am Chem. Soc: 1990, 112, 1123. Sakamoto, K.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1466.
23. Krushin, S.; Masuda, Y ; Matsushita, K.; Nakadaira, Y.; Ohashi, M. Tetrahedron Lett. 1990, 31, 6395.
24. Lee, Y. J.; Lee, C. P.; Jeon, Y. T.; Mariano, P. S.; Yoon, U. C.; Kim, D. U.; Kim, J. C.; Lee, J. G. Tetrahedron Lett. 1993, 34, 5855.
25. Jeon, Y. T.; Lee, C. P., Mariano, P S. J. Am. Chem. Soc. 1991, 113, 8847.
26. Kuivila, H. G.; Maxfield, P. L. J. Organomet. Chem. 1967, 10, 41.
27. Kanaoka, Y.; Migita, Y.; Koyama, K.; Sato, Y.; Nakai, H.; Mizoguchi, T. Tetrahedron Lett. 1973, 14, 1193.
28. Davidson, J. M. T. Organometallics 1987, 6, 644.
29. (a) Hasegawa, E.; Xu, W.; Mariano, P. S.; Yoon, U. C.; Kim, S. U. J. Am Chem. Soc. 1988, 109, 8089.
30. (b) Xu, W.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 1431.
31. Gold, E. H. J. Am. Chem. Soc. 1971, 93, 2793. Allworth, K. L.; El-Hamamy, A. A.; Hesabi, M. M.; Hill, J. J. Chem. Soc., Perkin Trans. 1 1980, 1671.
32. Gold, E. H. J. Am. Chem. Soc. 1971, 93, 2793. Allworth, K. L.; El-Hamamy, A. A.; Hesabi, M. M.; Hill, J. J. Chem. Soc., Perkin Trans. 1 1980, 1671.
33. The results of the current study with 14 match those found earlier by Kuivila (ref 14).
34. Kresge, A J. Pure Appl. Chem. 1991, 63, 213.
35. See: Cohen, S. G.; Davis, G. A.; Clark, W. D. K. J. Am. Chem. Soc. 1972, 94, 869 and references therein.
36. Bartrop, J. A.; Coyle, J. D. J. Am. Chem. Soc. 1968, 90, 6584.