Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes

Synlett

Volumn 1996, Issue 5, 1996, Pages 461-464

  Li, Yuanqiang ^a   Matsuda, Michio ^a   Thiemann, Thies ^b   Sawada, Tsuyoshi ^c   Mataka, Shuntaro ^c   Tashiro, Masashi ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c Institute of Advanced Material Study   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007243634     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5446     Document Type: Article

References (30)

1. Part of this work has been presented at the 68th Annual Spring Meeting of the Chemical Society of Japan, Tokyo 1994 (abstract 3J1 45, p. 1038).
2. M. Prochazka, Coll. Czech. Chem. Commun. 1965, 30, 1158; see also: J. L. Melles, H. J. Baecker, Recl. Trav. Chim. Pays-Bas 1953, 72, 491; W. Davies, F. C. James, J. Chem. Soc. 1954, 15; K. Okita, S. Kambara, Kogyo Kagaku Zasshi 1956, 59, 547; Chem. Abstr. 1958, 52, 3762.
3. M. Prochazka, Coll. Czech. Chem. Commun. 1965, 30, 1158; see also: J. L. Melles, H. J. Baecker, Recl. Trav. Chim. Pays-Bas 1953, 72, 491; W. Davies, F. C. James, J. Chem. Soc. 1954, 15; K. Okita, S. Kambara, Kogyo Kagaku Zasshi 1956, 59, 547; Chem. Abstr. 1958, 52, 3762.
4. M. Prochazka, Coll. Czech. Chem. Commun. 1965, 30, 1158; see also: J. L. Melles, H. J. Baecker, Recl. Trav. Chim. Pays-Bas 1953, 72, 491; W. Davies, F. C. James, J. Chem. Soc. 1954, 15; K. Okita, S. Kambara, Kogyo Kagaku Zasshi 1956, 59, 547; Chem. Abstr. 1958, 52, 3762.
5. M. Prochazka, Coll. Czech. Chem. Commun. 1965, 30, 1158; see also: J. L. Melles, H. J. Baecker, Recl. Trav. Chim. Pays-Bas 1953, 72, 491; W. Davies, F. C. James, J. Chem. Soc. 1954, 15; K. Okita, S. Kambara, Kogyo Kagaku Zasshi 1956, 59, 547; Chem. Abstr. 1958, 52, 3762.
6. M. Prochazka, Coll. Czech. Chem. Commun. 1965, 30, 1158; see also: J. L. Melles, H. J. Baecker, Recl. Trav. Chim. Pays-Bas 1953, 72, 491; W. Davies, F. C. James, J. Chem. Soc. 1954, 15; K. Okita, S. Kambara, Kogyo Kagaku Zasshi 1956, 59, 547; Chem. Abstr. 1958, 52, 3762.
7. K. Torssell, Acta Chem. Scand. (5er. B) 1976, 353.
8. A. M. Naperstkow, J. B. Macauly, M. J. Newlands, A. G. Fallis, Tetrahedron Lett. 1989, 30, 5077.
9. Y.-Q. Li, T. Thiemann, T. Sawada, M. Tashiro, J. Chem. Soc., Perkin Trans I 1994, 2323.
10. T. Thiemann, Y.-Q. Li, C. Thiemann, T. Sawada, Y. Nagano, M. Matsuda, S. Mataka, M. Tashiro, unpublished results.
11. T. Thiemann, Y.-Q. Li, S. Mataka, M. Tashiro, J. Chem. Res. 1995, (S) 384; (M) 2364-2379.
12. A non-aromatic or antiaromatic character of thiophene-S-oxides has been postulated by W. L. Mock (see ref. 9). A number of molecular calculations have followed: cf. J. A. Hashmall, V. Horak, L. E. Khoo, C. O. Quicksall, M. K. Sun, J. Am. Chem. Soc. 1981, 103, 289; I. Rozas, J. Phys. Org. Chem. 1992, 5, 74.
13. A non-aromatic or antiaromatic character of thiophene-S-oxides has been postulated by W. L. Mock (see ref. 9). A number of molecular calculations have followed: cf. J. A. Hashmall, V. Horak, L. E. Khoo, C. O. Quicksall, M. K. Sun, J. Am. Chem. Soc. 1981, 103, 289; I. Rozas, J. Phys. Org. Chem. 1992, 5, 74.
14. W. L. Mock, J. Am. Chem. Soc. 1970, 92, 7610; P. J. Fagan, W. A. Nugent, J. Am. Chem. Soc. 1988, 110, 2310; F. Meier-Brocks, E. Weiss, J. Organomet. Chem. 1993, 33, 453. For all of the isolated thiophene-S-oxides it has been noted that large substituents in positions 2,5 are necessary for the stability of the compounds; see also ref. 11 and 12.
15. W. L. Mock, J. Am. Chem. Soc. 1970, 92, 7610; P. J. Fagan, W. A. Nugent, J. Am. Chem. Soc. 1988, 110, 2310; F. Meier-Brocks, E. Weiss, J. Organomet. Chem. 1993, 33, 453. For all of the isolated thiophene-S-oxides it has been noted that large substituents in positions 2,5 are necessary for the stability of the compounds; see also ref. 11 and 12.
16. W. L. Mock, J. Am. Chem. Soc. 1970, 92, 7610; P. J. Fagan, W. A. Nugent, J. Am. Chem. Soc. 1988, 110, 2310; F. Meier-Brocks, E. Weiss, J. Organomet. Chem. 1993, 33, 453. For all of the isolated thiophene-S-oxides it has been noted that large substituents in positions 2,5 are necessary for the stability of the compounds; see also ref. 11 and 12.
17. I. Erdelmeier, P. Pouzet, D. M. Dansette, P. Ginderow, J. P. Mornon, D. Mansuy, presented at 16th International Symposium on the Organic Chemistry of Sulfur (ISOCS) in Merseburg 1994, Book of Abstracts, p. 333.
18. P. Pouzet, I. Erdelmeier, P. Ginderow, J. P. Mornon, D. M. Dansette, D. Mansuy, J. Chem. Soc., Chem. Commun. 1995, 473.
19. M. Higaki, N. Furukawa, Book of Abstracts, 24th Congress of Heterocyclic chemistry, Osaka, Japan, 1993, p. 277.
20. Cf. M. S. Raasch, J. Org. Chem. 1980, 45, 856; P. H. Benders, D. N. Reinhoudt, W. P. Trompenaars, 'Cycloaddition Reactions of Thiophenes, Thiophene-1-oxides, and Thiophene-1,1-dioxides' In The Chemistry of Heterocyclic Compounds (S. Gronowitz, ed.) 1985, 44, 713.
21. Cf. M. S. Raasch, J. Org. Chem. 1980, 45, 856; P. H. Benders, D. N. Reinhoudt, W. P. Trompenaars, 'Cycloaddition Reactions of Thiophenes, Thiophene-1-oxides, and Thiophene-1,1-dioxides' In The Chemistry of Heterocyclic Compounds (S. Gronowitz, ed.) 1985, 44, 713.
22. Cf. J. Das, R. Kubela, G. A. MacAlpine, Z. Stojanic, Z. Valenta, Can. J. Chem. 1979, 57, 3308; T. Thiemann, S. Kohlstruk, G. Schwaer, A. de Meijere, Tetrahedron Lett. 1991, 32, 3483.
23. Cf. J. Das, R. Kubela, G. A. MacAlpine, Z. Stojanic, Z. Valenta, Can. J. Chem. 1979, 57, 3308; T. Thiemann, S. Kohlstruk, G. Schwaer, A. de Meijere, Tetrahedron Lett. 1991, 32, 3483.
24. +, 11), 141 (16), 123 (77).
25. +), 164 (19.5).
26. +-SO, 47), 268 (59).
27. A. W. McCulloch, D. G. Smith, A. G. McInnes, Can. J. Chem. 1973, 51, 4126.
28. For typical examples of oxidations of sulfoxides to sulfones under PTC conditions see: D. Scholz, Monatsh. Chem. 1981, 112, 241; D. G. Lee, N. Srinivasan, Sulfur Lett. 1982, 1, 1.
29. For typical examples of oxidations of sulfoxides to sulfones under PTC conditions see: D. Scholz, Monatsh. Chem. 1981, 112, 241; D. G. Lee, N. Srinivasan, Sulfur Lett. 1982, 1, 1.
30. C. Thiemann, T. Thiemann, Y.-Q. Li, T. Sawada, Y. Nagano, M. Tashiro, Bull. Chem. Soc. Jpn. 1994, 67, 1886.