Photocycloaddition of arylethenes to 2-substituted-l,4-naphthoquinoncs and reactions of the cyclobutane adduct isomers

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 7, 2000, Pages 1149-1155

  Cleridou, Stephanie ^a   Covell, Christopher ^a   Gadhia, Anita ^a   Gilbert, Andrew ^a   Kamonnawin, Patcharawalai ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DIMERS; ISOMERS; OLEFINS; PHOTOREACTIVITY; SUBSTITUTION REACTIONS;

PHOTOCYCLOADDITION; PHOTOSUBSTITUTION;

ADDITION REACTIONS;

EID: 0034615796     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909384b     Document Type: Article

References (33)

1. See references in (a) W. M. Horspool, "Enone Cycloadditions and Rearrangements: Photoreactions of Dienones and Quinones" in Specialist Periodical Report on Photochemistry, The Royal Society of Chemistry, Cambridge, 1970-1999, vol. 1-30 inclusive;
2. (b) K. Maruyama and A. Osuka, "Recent Advances in the Photochemistry of Quinones," in The Chemistry of Qitinonoid Compounds, vol. II, ed. S. Patai and Z. Rappoport, Wiley, New York, 1988;
3. M. Bruce, "Photochemistry of Quinones," in The Chemistry of Quinonoid Compounds, vol. I, ed. S. Patai, Wiley, New York, 1974, p. 465.
4. See, for example, D. Bryce-Smith, A. Gilbert and M. G. Johnson, J. Chem. Soc, C, 1967, 383;
5. N. J. Bunce and M. Hadley, Can. J. Cliem., 1975, 53, 3240;
6. R. M. Wilson, S. W. Wunderly, T. F. Walsh, A. K. Musser, R. Outcalt, F. Geiser, S. K. Gee, W. Brabender, L. Yerino, T. T. Conrad and G. A. Tharp, J. Am. Chem. Soc., 1982, 104,4429;
7. K. A. Schnapp, R. M. Wilson, D. M. Ho, R. A. Caldwell and D. Creed, J. Am. Client. Soc., 1990, 112, 3700;
8. D. Bryce-Smith, E. H. Evans, A. Gilbert and H. M. McNeil, J. Chem. Soc., Perkin Trans. 2, 1991, 1587;
9. M. T. Crimmins and T. L. Reinhold, Org. React.,1993,44,297.
10. T. Oshima, Y. Nakajima and S. Kumazaki, Heterocydes, 1996, 43, 619;
11. M. Cristl and M. Braun, Licbigs Ann.lRecl, 1997, 1135;
12. E. Bosch, S. M. Hubig and J. K. Kochi, J. Am. Chem. Soc., 1998, 120, 386;
13. E. Bosch, S. M. Hubig, S. V. Lindeman and J. K. Kochi, J. Am. Chem. Soc., 1998,120, 592.
14. N. J. Bunce, J. E. Ridler and M. C. Zerner, Theor. Chim. Acta., 1977, 45, 283.
15. D. Bryce-Smith, E. H. Evans, A. Gilbert and H. S. McNeil, J. Chem. Soc., Perkin Trans, 1, 1992, 485.
16. A. Kuboyama, Bull. Chem. Soc. Jpn., 1960, 33, 1027;
17. P. E. Stevenson, J. Mol. Spectrosc, 1965, 17, 58.
18. T. Otsuki, Bull. Chem. Soc. Jpn., 1976, 49, 2596.
19. K. Kobayashi, H. Shimizu, A. Sasaki and H. Suginome, J. Org. Chem., 1993, 58, 4614.
20. K. Kobayashi, H. Takeuchi, S. Seko, Y. Kanno, S. Kujime and H. Suginome, Helv. Chim. Acta, 1993, 76, 2942.
21. H. Suginome, K. Kobayashi, A. Konishi, H. Minakawa and H. Sakurai,./ Chem. Soc., Chem. Commun., 1993, 807.
22. M. P. Cava and R. L. Shirley, J. Org. Chem., 1961, 26, 2212;
23. P. J. Garratt and R. Zahler, Tetrahedron Lett., 1979,35, 73.
24. W. S. Murphy and D. Neville, Tetrahedron Lett., 1996, 52, 9397.
25. T. Naito, Y. Makita, S. Yazaki and C. Kaneko, Chem. Pharm. Bull., 1986, 34, 1505.
26. K. Maruyama and H. Imahori, J. Chem. Soc., Perkin Trans. 2, 1990, 257; and references therein.
27. K. Maruyama, T. Otsuki and S. Tai, J. Org. Chem., 1985, 50, 52.
28. K. Maruyama, T. Otsuki and K. Mitsui, Bull. Chem. Soc. Jpn., 1976, 49, 3361.
29. J. H. Xu, Y. C. Song, Z. G. Zhang, L. C. Wang and J. W. Xu, Tetrahedron, 1994,50, 1199.
30. J. Conant and L. F. Fieser, J. Chem. Soc, 1924, 1870.
31. H. Senboku, Y. Kajizuka, K. Kobayashi, M. Tokuda and H. Suginome, Heterocydes, 1997,44, 341.
32. C. Covell, A. Gilbert and C. Richter, J. Chem. Res., 1998, 316.
33. We are grateful to Professor Murphy for this personal communication.