trans-Stilbene-Amine Exciplexes. Photochemical Addition of Secondary and Tertiary Amines to Stilbene

Journal of the American Chemical Society

Volumn 99, Issue 24, 1977, Pages 7991-7996

  Lewis, Frederick D ^a   Ho, Tong Ing ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847089512     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00466a035     Document Type: Article

References (42)

1. a) O. L. Chapman and R. D. Lura, J. Am. Chem. Soc., 92, 6352 (1970);
2. J. Saltiel, J. T. D'Agostino, O. L. Chapman, and R. D. Lura, J. Chem. Soc., 93, 2804 (1971);
3. O. L. Chapman, R. D. Lura, R. M. Owens, E. D. Plank, S. C. Shim, D. R. Arnold, and L. B. Gillis, Can J. Chem., 50, 1984 (1972);
4. H. M. Rosenberg, R. Rondeau, and P. Servė, J. Org. Chem., 34, 471 (1969);
5. H. M. Rosenberg and M. P. Serve, Serve, 36, 3015 (1971);
6. M. P. Servė, Can. J. Chem., 50, 3744 (1972).
7. F. D. Lewis, R. H. Hirsch, P. M. Roach, and D. E. Johnson, J. Am. Chem. Soc., 98, 8438(1976).
8. a) B. S. Green and M. Rejto, J. Org. Chem., 39, 3285 (1974);
9. F. D. Lewis, C. E. Hoyle, and D. E. Johnson, unpublished results.
10. a) F. D. Lewis and R. H. Hirsch, Tetrahedron Lett., 4947 (1973);
11. F. D. Lewis, C. E. Hoyle and D. E. Johnson, J. Am. Chem. Soc., 97,3267 (1975);
12. F. D. Lewis and R. H. Hirsch, Tetrahedron Lett., 2651 (1975);
13. J. Am Chem. Soc., 98, 5914 (1976).
14. a) F. D. Lewis and C. E. Hoyle, J. Am. Chem. Soc., 98, 4338 (1976);
15. (b) J. Am. Chem. Soc., 99, 3779 (1977).
16. a) M. Kawanisi and K. Matsunaga, J. Chem. Soc., Chem. Commun., 313 (1972);
17. T. Kubota and H. Sakurai, Chem. Lett., 923 (1972);
18. (c) Chem. Lett., 1249 (1972);
19. A. Couture, A. Lablache-Combier, and H. Ofenberg, Tetrahedron, 21, 2023 (1975).
20. a) D. J. S. Birch and J. B. Birks, Chem. Phys. Lett., 38, 432 (1976);
21. J. L. Charlton and J. Saltiel, J. Phys. Chem., in press.
22. Similar products have been observed for styrene and other 1-phenylalkenes with tertiary amines: R. C. Cookson, S. M. de B. Costa, and J. Hudec, Chem Commun., 753 (1969).
23. a) M. J. Gibian and R. C. Corley, J. Am. Chem. Soc., 94, 4178 (1972);
24. W. H. Urry and O. O. Juveland, J. Am. Chem. Soc., 80, 3322 (1958).
25. N. Mataga, Y. Torihashi, and K. Ezumi, Theor. Chim. Acta, 2, 158 (1964).
26. a) H. Beens, H. Knibbe, and A. Weller, J. Chem. Phys., 47, 1183 (1967);
27. D. Gupta and S. Basu, J. Photochem., 4, 307 (1975).
28. B. Stevens, Adv. Photochem., 8, 161 (1971).
29. a) H. Knibbe, K. Röllig, F. P. Schäfer, and A. Weller, J. Chem. Phys., 47, 1184 (1967);
30. N. Mataga, Y. Taniguchi, and Y. Nishina, Bull. Chem. Soc. Jpn., 45, 764 (1972).
31. F. D. Lewis and C. E. Hoyle, J. Am. Chem. Soc., 97, 5950 (1975).
32. a) N. C. Yang, D. M. Shold, and B. Kim, J. Am. Chem. Soc., 98, 6587 (1976);
33. J. Saltiel, D. E. Townsend, B. D. Watson, P. Shannon, and S. L. Finson, J. Am. Chem. Soc., 99, 884 (1977).
34. N. C. Yang and J. Libman, J. Am. Chem. Soc., 95, 5783 (1973).
35. F. Nolting, A. Weller, and K. A. Zachariasse, Vlth IUPAC Symposium on Photochemistry, Aix-en-Provence, France, July 1977, p 356.
36. a) D. Rehm and A. Weller, Isr. J. Chem., 8, 259 (1970);
37. T. R. Evans, J. Am. Chem. Soc., 93, 2081 (1971);
38. J. B. Guttenplan and S. G. Cohen, J. Am. Chem. Soc., 94, 4041 (1972).
39. J. J. McCullough, R. C. Miller, D. Fung, and W. S. Wu, J. Am. Chem. Soc., 95, 3228(1973).
40. J. R. Roberts and K. U. Ingold, J. Am. Chem. Soc., 95, 3228 (1973).
41. J. C. Dalton and J. J. Snyder, J. Am. Chem. Soc., 97, 5192 (1975).
42. D. P. Wyman, J. Org. Chem., 27, 3712 (1962).