Diene–dienophile dual reactivity of conjugated vinyl sulfines

Abstract

The discovery of a new and facile synthesis of α,β-unsaturated thioaldehyde S-oxides has enabled the exploration of the diene–dienophile reactivity of these novel heterocumulenes. Unlike some previous reports, the addition of (Z )-β,β-dimethylvinyl and (Z )-β-styryl sulfines to either cyclic or acyclic dienes proceeds in a non-stereospecific manner, yielding three stereoisomers. In contrast, the latter sulfine reacts as a diene with norbornene and other dienophiles to give a single product.

References

1. S. Braverman and Y. Stabinsky, J. Chem. Soc., Chem. Commun., 1967, 270.
2. Also known as the Mislow–Braverman–Evans rearrangement, see A. Hassner and C. Stumer, in Organic Syntheses Based on Name Reactions and Unnamed Reactions, Pergamon, Oxford, 1994, p. 266.
3. S. Braverman, Rearrangements of Sulfoxides in Chemistry of Sulfones and Sulfoxides, eds. S. Patai, Z. Rappoport and C. J. M. Stirling, Wiley, New York, 1988, ch. 14.
4. S. Braverman, D. Grinstein and H. E. Gottlieb, Tetrahedron Lett., 1994, 35, 953; S. Braverman, D. Grinstein and H. E. Gottlieb, Tetrahedron, in press.
5. (a) B. Zwanenburg, Recl. Trav. Chim. Pays-Bas, 1982, 101, 1; (b) B. Zwanenburg and B. G. Lenz, in Houben-Weyl Methoden der Organischen Chemie, Band E 11/2, Organische Schwefelverbindugen, Georg Thieme Verlag, Stuttgart, 1985, p. 911; (c) B. Zwanenburg, Rev. Heteratom. Chem., 1988, 1, 218; (d) B. Zwanenburg, Phosphorus, Sulfur Silicon Relat. Elem., 1989, 43, 1; (e) E. Block, in Organic Sulfur Chemistry, eds. R. Kh. Freidlina and A. E. Skorova, Pergamon, Oxford, 1981, p. 15.
6. B. Zwanenburg, unpublished results [cf. ref. 5(a)]; T. Saito, N. Shibahara and S. Motoki, Tetrahedron Lett., 1983, 24, 4435; D. H. R. Barton, L. S. L. Choi, R. H. Hesse, M. M. Pechet and C. Wilshire, J. Chem. Soc., Chem. Commun., 1977, 1529.
7. M. Franck-Neumann and J. J. Lohmann, Tetrahedron Lett., 1979, 2397.
8. C. N. Skold and R. H. Schlessinger, Tetrahedron Lett., 1970, 791; W. J. M. van Tilborg, Recl. Trav. Chim. Pays-Bas, 1976, 95, 140.
9. T. Karakasa and S. Motoki, Tetrahedron Lett., 1979, 3961; T. Karakasa, H. Ohmura and S. Motoki, Chem. Lett., 1980, 825.
10. S. Braverman, P. F. T. M. van Asten, J. B. van der Linden and B. Zwanenburg, Tetrahedron Lett., 1991, 31, 3867; J. B. van der Linden, P. F. T. M. van Asten, S. Braverman and B. Zwanenburg, Recl. Trav. Chim. Pays-Bas, 1995, 114, 51.
11. J. Strating, L. Thijs and B. Zwanenburg, Recl. Trav. Chim. Pays-Bas, 1964, 83, 631; A. M. Hamid and S. Trippett, J. Chem. Soc. C, 1968, 1617; E. Block, L. K. Revelle and A. A. Bazzi, Tetrahedron Lett., 1980, 1277.
12. B. F. Bonini, G. Mazzanti, P. Zani, G. Maccagnani, A. Battaglia and P. Giorgianni, J. Chem. Soc., Chem. Commun., 1986, 964; G. Barbaro, A. Battaglia, P. Giorgianni, B. F. Bonini, G. Maccagnani and P. Zani, J. Org. Chem., 1990, 55, 3744; 1991, 56, 2512; B. F. Bonini, Phosphorus, Sulfur Silicon, Relat. Elem., 1993, 74, 31.
13. J. B. Grutzner, M. Jautelat, J. B. Dence, R. A. Smith and J. D. Roberts, J. Am. Chem. Soc., 1970, 92, 7107.
14. PCModel, Serena Software, Box 3076, Bloomington, IN 47402-3076, USA.
15. S. Braverman and Z. Lior, Tetrahedron Lett., 1994, 35, 6725.