Intramolecular photo[4+2]cycloaddition of an enone with a benzene ring

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 1, 1997, Pages 77-84

  Kishikawa, Keiki ^a   Akimoto, Satoshi ^a   Kohmoto, Shigeo ^a   Yamamoto, Makoto ^a   Yamada, Kazutoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002559999     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a601710j     Document Type: Article

References (34)

1. (a) J. Cornelisse, Chem. Rev., 1993, 93, 615;
2. (b) P. A. Wender, L. Shiggel and J. M. Nuss, Org. Photochem., 1989, 10, 357;
3. (c) P. J. Wagner, Acc. Chem. Res., 1989, 22, 83;
4. (d) H. Aoyama, Y. Arata and Y. Omote, J. Chem. Soc., Chem. Commun., 1990, 736;
5. (e) N. Al-Jalel and A. Gilbert, Recl. Trav. Chim. Pays-Bas, 1990, 109, 21;
6. (f) P. A. Wender and M. A. deLong, Tetrahedron Lett., 1990, 31, 5429;
7. (g) A. Gilbert and P. W. Rodwell, J. Chem. Soc., Perkin Trans. 1, 1990, 932;
8. (h) D. Bryce-Smith and A. Gilbert, Tetrahedron, 1977, 33, 2459;
9. (i) D. Bryce-Smith, A. Gilbert, B. H. Orger and H. M. Tyrrell, J. Chem. Soc., Chem. Commun., 1974, 334;
10. (j) D. Bryce-Smith, B. Foulger, J. Forrester. A. Gilbert, B. H. Orger and H. M. Tyrrell, J. Chem. Soc., Perkin Trans. 1, 1980, 55;
11. (k) A. Gilbert, G. N. Taylor and M. W. bin Samsudin, J. Chem. Soc., Perkin Trans. 1, 1980, 869;
12. (l) J. Mattay, H. Leismann and H. D. Scharf, Chem. Ber., 1979, 112, 577;
13. (m) H. G. Heine and W. Hartmann, Angew. Chem., Int. Ed. Engl., 1975, 14, 698;
14. (n) M. F. Mirbach, M. J. Mirbach and A. Saus, Tetrahedron Lett., 1977, 959.
15. D. Bryce-Smith, B. Foulger, J. Forrester and A. Gilbert, J. Chem. Soc., Chem. Commun., 1972, 664;
16. J. C. Berridge, J. Forrester, B. Foulger and A. Gilbert, J. Chem. Soc., Perkin Trans. 1, 1980, 2425.
17. A. Gilbert and P. W. Rodwell, J. Chem. Soc., Perkin Trans. 1, 1990, 931.
18. H. D. Scharf, H. Leismann, W. Erb and J. Aretz, Pure Appl. Chem., 1975, 41, 581.
19. G. O. Schenck, J. Kuhls and C. H. Krauch, Justus Liebigs Ann. Chem., 1966, 693, 20;
20. K. Kraft. G. Koltzenburg and G. O. Schenck, Tetrahedron Lett., 1965, 353;
21. T. S. Cantrell, J. Org. Chem., 1974, 39, 3063.
22. The MM2 force field in Chem3D (Cambridge Soft, Co.) was used for the calculation. Cf. U. Bunkert and N. L. Allinger, Molecular Mechanics, ACS, Washington, DC, USA. 1982;
23. J. W. Ponder, J. Comput. Chem., in preparation.
24. D. Bryce-Smith and A. Gilvert, Tetrahedron, 1976, 32, 1309.
25. G. Himbert, K. Kiehl and G. Maas, J. Chem. Soc., Chem. Commun., 1984, 900;
26. L. A. M. Turkenburg, P. M. L. Blok, W. H. De Wolf and F. Bickelhaupt, Angew. Chem., Int. Ed. Engl., 1982, 21, 298;
27. A. F. Murad, J. Kleinschroth and H. Hopf, Angew. Chem., Int. Ed. Engl., 1980, 19, 389.
28. M. Wollenweber, H. Fritz, G. Rihs and H. Prinzbach, Chem., Ber., 1991, 124, 2465;
29. M. Mintas, D. I. Schuster and P. G. Willard, Tetrahedron, 1988, 44, 6001.
30. J. Bregmen, K. Osaki, G. M. J. Schmidt and F. I. Sontag, J. Chem. Soc., 1964, 2021.
31. W. M. Hardham and G. S. Hammond, J. Am. Chem. Soc., 1967, 89, 3200.
32. S. Kohmoto, T. Kreher, Y. Miyaji, M. Yamamoto and K. Yamada, J. Org. Chem., 1992, 57, 3490.
33. J. S. Bradshaw, J. Org. Chem., 1966, 31, 3974.
34. T. S. Lee, S. J. Lee and S. C. Shim, J. Org. Chem., 1990, 55, 4544.