Photochemical Michael reaction of silyl enol ethers with 2′-nitro-and 2′,2′-dicyanostyrenes

Journal of the Chemical Society. Perkin Transactions 2

Volumn 5, Issue , 1996, Pages 939-941

  Ramkumar, D ^a   Sankararaman, S ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345955304     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960000939     Document Type: Article

References (36)

1. (a) H. O. House, Modern Synthetic Reactions, The Benjamin Cummings, Menlo Park, 1972, 2nd edn., pp. 595-621;
2. (b) M. E. Jung, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, New York, 1991, vol. 4, pp. 1-68.
3. (a) T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 1977, 16, 817;
4. (b) T. Mukaiyama and M. Murakami, Synthesis, 1987, 1043;
5. (c) T. Mukaiyama, Challenges in Synthetic Organic Chemistry, Clarendon Press, Oxford, 1990, pp. 177-213;
6. (d) C. Gennari in ref. I(b), vol. 2, pp. 629-660.
7. (a) C. Pac, K. Mizuno, H. Okamoto and H. Sakurai, Synthesis, 1978, 589;
8. (b) M. Mitani and Y. Osakaba, J. Chem. Soc., Chem. Commun., 1994, 1759.
9. (a) L. Mathew, B. Varghese and S. Sankararaman, J. Chem. Soc., Perkin Trans. 2, 1993, 2399;
10. (b) L. Mathew and S. Sankararaman, J. Org. Chem., 1993, 58, 7576.
11. (a) D. J. Cowley, J. Chem. Soc., Perkin Trans. 2, 1975, 1576;
12. (b) E. A. Brande, E. R. H. Jones and G. G. Rose, J. Chem. Soc., 1947, 1104.
13. (a) T. Mukaiyama, M. Tamura and S. Kobayashi, Chem. Lett., 1986, 1017;
14. (b) M. Miyashita, T. Yanami, T. Kumazawa and A. Yoshikoshi, J. Am. Chem. Soc., 1984, 106, 2149;
15. (c) D. Seebach and M. A. Brook, Helv. Chim. Acta, 1985, 68, 319;
16. (d) M. A. Brook and D. Seebach, Can. J. Chem., 1987, 65, 836;
17. (e) S. J. Blarer, W. B. Schweizer and D. Seebach, Helv. Chim. Acta., 1982, 65, 1637.
18. E. J. Corey, J. D. Bass, R. LaMathieu and R. B. Mitra, J. Am. Chem. Soc., 1964, 86, 5570.
19. (a) D. J. Hastings and A. C. Weedon, J. Am. Chem. Soc., 1991, 113, 8525;
20. (b) P. Krug, A. Rudolph and A. C. Weedon, Tetrahedron Lett., 1993, 34, 7221.
21. R. Huisgen, Acc. Chem. Res., 1977, 10, 117, 199 and references cited therein.
22. (a) D. B. Miller, P. W. Flanagen and H. Shechter, J. Org. Chem., 1976, 41, 2112;
23. (b) J. A. Souza, J. Weinstein and A. L. Bluhm, J. Org. Chem., 1969, 34, 3320.
24. A. Lamola and N. J. Turro, Energy Transfer and Organic Photochemistry, Interscience, New York, 1969, p. 240.
25. H. O. House, L. J. Czuba, M. Gall and H. D. Olmstaed, J. Org. Chem., 1969, 34, 2324.
26. Vogel's Textbook of Practical Organic Chemistry, ELBS and Longman, London, 5th edn., 1991, p. 1035.
27. K. Mitsunobu, H. Oku, T. Shono and T. Nakanishi, Takamine Kenkyusho Nempo, 1961, 13, 205
28. (Chem. Abstr., 1962, 57, 16450g).
29. M. C. Moorjani and G. K. Trivedi, Ind. J. Chem., 1978, 16B, 405.
30. B. B. Corson and R. W. Stoughton, J. Am. Chem. Soc., 1928, 50, 2825.
31. H. G. Sturz and C. R. Noller, J. Am. Chem. Soc., 1949, 71, 2949.
32. N. L. Duraki and P. Allen, Jr., Org. Synth. Coll. Vol. I, John Wiley, London, 1932, p. 77.
33. M. E. McEntee and A. R. Pinder, J. Chem. Soc., 1957, 4419.
34. R. A. Wohl, Synthesis, 1974, 38.
35. (a) V. Geetha Saraswathy and S. Sankararaman, J. Org. Chem., 1995, 60, 5024;
36. (b) see also refs. 6 and 15.