Desilylation of (Z )-α-dimethylphenylsilyl vinyl sulfides with fluoride ion: ¹ revised mechanism for phenyl group migration in substrates containing an electron-withdrawing group β to the sulfur

Abstract

A detailed investigation of the desilylation of (Z )-α-dimethylphenylsilyl vinyl sulfides with fluoride ion has shown that in substrates containing an electron-withdrawing group β to the sulfur, phenyl group migration occurs as a result of a fluoride ion catalyzed retro-Michael reaction.

References

1. B. F. Bonini, M. Comes Franchini, M. Fochi, G. Mazzanti, F. Peri and A. Ricci, J. Chem. Soc., Perkin Trans. 1, 1996, 2803.
2. (a) B. Th. Gröbel and D. Seebach, Chem. Ber., 1977, 110, 852; (b) R. D. Miller and R. Hassig, Tetrahedron Lett., 1984, 25, 5351; (c) B. Harirchian and P. Magnus, J. Chem. Soc., Chem. Commun., 1977, 522; (d) F. Cooke, R. Moerck, J. Schwindeman and P. Magnus, J. Org. Chem., 1980, 45, 1046.
3. (a) K. S. Kyler and D. S. Watt, J. Org. Chem., 1981, 46, 5182; (b) T. Mandai, M. Kohama, H. Sato, M. Kawada and J. Tsuji, Tetrahedron, 1990, 46, 4553.
4. (a) P. Magnus and D. A. Quagliato, Organometallics, 1982, 1, 1240; (b) P. Magnus and D. A. Quagliato, J. Org. Chem., 1985, 50, 1621.
5. B. F. Bonini, M. Comes Franchini, M. Fochi, G. Mazzanti and A. Ricci, Tetrahedron, 1996, 52, 4803.
6. B. F. Bonini, M. Comes Franchini, M. Fochi, G. Mazzanti and A. Ricci, Tetrahedron, 1997, 53, 7897.
7. For the conversion of acetals into thioacetals see Corey and Seebach, Angew. Chem. Int. Ed. Engl., 1965, 4, 1075.
8. J. March, Advanced Organic Chemistry, J. Wiley and Sons, New York, 1985, III edn., p. 687.
9. D. P. Cox, J. Terpinski and W. Lawrynwicz, J. Org. Chem., 1989, 49, 3216.
10. B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Perkin Trans 1, 1989, 2083.
11. I. Fleming, T. W. Newton and F. Roessler, J. Chem. Soc., Perkin Trans 1, 1981, 2527.