First [4 + 2] cycloaddition of 1-phenyl-1-benzothiophenium salts with dienes

Organic Letters

Volumn 1, Issue 2, 1999, Pages 257-259

  Kitamura, Tsugio ^a   Zhang, Bian Xiang ^a   Fujiwara, Yuzo ^a   Shiro, Motoo ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000076532     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990587q     Document Type: Article

References (23)

1. For recent reviews, see: (a) Nakayama, J. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Elsevier: Oxford, U.K., 1996; 607-677.
2. (b) Rajappa, S.; Natekar, M. V. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Elsevier: Oxford, U.K., 1996; Vol. 2, pp 491-605.
3. (a) Brumlik, G. C.; Kosak, A. I.; Pitcher, R. J. Am. Chem. Soc. 1964, 86, 5360-5361.
4. (b) Acheson, R. M.; Harrison, D. R. J. Chem. Soc., Chem. Commun. 1969, 724.
5. (c) Acheson, R. M.; Harrison, D. R. J. Chem. Soc. C 1970, 1764-1784.
6. (d) Acheson, R. M.; Stubbs, J. K. J. Chem. Soc., Perkin Trans. 1 1972, 899-903.
7. (e) Hogeveen, H.; Kellogg, R. M.; Kuindersma, K. A. Tetrahedron Lett. 1973, 3929-3932.
8. (f) Heldeweg, R. F.; Hogeveen, H. Tetrahedron Lett. 1974, 75-78.
9. (g) Acheson, R. M.; Prince, R. J.; Procter, G.; Wallis, J. D.; Watkin, D. J. J. Chem. Soc., Perkin Trans. 2 1981, 266-269.
10. (a) Kitamura, T.; Kawasato, H.; Kobayashi, S.; Taniguchi, H. Chem. Lett. 1986, 339-342.
11. (b) Kitamura, T.; Takachi, T.; Kawasato, H.; Taniguchi, H.; Shiro, M. Tetrahedron 1993, 49, 5055-5066.
12. (a) Kitamura, T.; Takachi, T.; Kawasato, H.; Kobayashi, S.; Taniguchi, H. Tetrahedron Lett. 1989, 30, 7445-7446.
13. (b) Kitamura, T.; Takachi, T.; Miyaji, M.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1994, 1907-1911.
14. (a) Kitamura, T.; Yamane, M.; Furuki, R.; Taniguchi, H.; Shiro, M. Chem. Lett. 1993, 1703-1706.
15. (b) Kitamura, T.; Yamane, M.; Zhang, B.-X.; Fujiwara, Y. Bull. Chem. Soc. Jpn. 1998, 71, 1215-1219.
16. (a) Kitamura, T.; Miyaji, M.; Soda, S.; Taniguchi, H. J. Chem. Soc. Chem. Commun. 1995, 1375-1374.
17. (b) Kitamura, T.; Soda, S.; Morizane, K.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 2 1996, 473-474.
18. Kaftory, M.; Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1985, 107, 1701-1709.
19. Some recent reports on the theoretical study of 1-methylthiophenium ion suggest that thiophenium ion acts as a diene to undergo [4 + 2] cycloaddition, see: (a) ref 2g.
20. (b) Zhang, S.-Z.; Sato, S.; Horn, E.; Furukawa, N. Heterocycles 1998, 48, 227-234.
21. (c) Jursic, B. S.; Zdravkovski, Z.; Whittenburg, S. L. J. Chem. Soc., Perkin Trans. 2 1996, 455-459.
22. 3) δ = 59.8, 74.1, 90.0, 93.6, 122.0, 122.6, 125.9, 126.7, 127.9, 128.7, 128.9, 129.10, 129.12, 129.3, 129.466, 129.474, 129.7, 130.3, 130.7, 131.6, 131.8, 133.2, 134.1, 134.2, 134.9, 141.0, 143.8, 144.9.
23. w = 0.096.