Photochemistry of heteroaromatics - A novel photocycloaddition of 2-alkoxy-3-cyanopyridines with methacrylonitrile

Chemical Communications

Volumn , Issue 11, 1996, Pages 1349-1350

  Sakamoto, Masami ^a   Sano, Takeru ^a   Takahashi, Masaki ^a   Yamaguchi, Kentaro ^a   Fujita, Tsutomu ^a   Watanabe, Shoji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002538055     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001349     Document Type: Article

References (12)

1. D. Bryce-Smith and A. Gilbert, Tetrahedron, 1976, 32, 1309.
2. A. Gilbert, Synthetic Organic Photochemistry, ed. W. H. Horspool, Plenum: New York, 1984.
3. P. A. Wender, L. Siggel and J.M. Nuss, Organic Photochemistry, ed. A. Padwa, Marcel Dekker, New York and Basel, 1991, vol. 10, pp. 357.
4. J. Cornelisse, Chem. Rev., 1993, 93, 615.
5. For the photocycloaddition of pyridines with alkenes, only one example has been reported. Pentafluoropyridine reacts with ethylene at the C(3)-C(4) bond leading to cyclobutane; see M. G. Barlow, D. E. Brown and R. N. Haszeldine, J. Chem. Soc., Chem. Commun., 1977, 669.
6. I. Saito, K. Kanehira, K. Shimozono and T. Matsuura, Tetrahedron Lett., 1980, 21, 2737; R. Bernardi, T. Caronna, S. Morrocchi and P. Traldi, Tetrahedron Lett., 1981, 22, 155.
7. I. Saito, K. Kanehira, K. Shimozono and T. Matsuura, Tetrahedron Lett., 1980, 21, 2737; R. Bernardi, T. Caronna, S. Morrocchi and P. Traldi, Tetrahedron Lett., 1981, 22, 155.
8. M. Sakamoto, M. Kimura, T. Fujita, T. Nishio, I. Iida and S. Watanabe, J. Am. Chem. Soc., 1991, 113, 5859; M. Sakamoto, T. Takahashi, M. Kimura, M. Fujihira, T. Fujita, I. Iida, T. Nishio and S. Watanabe, J. Org. Chem., 1994, 59, 5117.
9. M. Sakamoto, M. Kimura, T. Fujita, T. Nishio, I. Iida and S. Watanabe, J. Am. Chem. Soc., 1991, 113, 5859; M. Sakamoto, T. Takahashi, M. Kimura, M. Fujihira, T. Fujita, I. Iida, T. Nishio and S. Watanabe, J. Org. Chem., 1994, 59, 5117.
10. The formation of the transpositional isomer is reasonably explained in terms of a 1,3-shift via Dewar pyridines or azaprizmanes; see S. Captlain and A. Lablache-Combier, J. Chem. Soc., Chem. Commun., 1970, 1247 and R. D. Chambers and R. Middleton, J. Chem. Soc., Perkin Trans. I, 1977, 1500.
11. The formation of the transpositional isomer is reasonably explained in terms of a 1,3-shift via Dewar pyridines or azaprizmanes; see S. Captlain and A. Lablache-Combier, J. Chem. Soc., Chem. Commun., 1970, 1247 and R. D. Chambers and R. Middleton, J. Chem. Soc., Perkin Trans. I, 1977, 1500.
12. Similar transformations are documented for photocycloadducts of benzenes with alkenes, leading to cyclooctatrienes and bicyclo[4.2.0]octadienes; see P. J. Wagner and K. Nahm, J. Am. Chem. Soc., 1987, 109, 4404.