Effect of a cobalt(II) complex on the radical reaction of vinyl type sulfides. A ‘radico-catalysis’

Abstract

Vinyl type sulfides show increased radicophilicity at the β-position via the coordination to a cobalt(II) complex, and hence the balance between Smiles rearrangement and an ortho-substitution, in vinyl type sulfides having an intramolecular alkyl radical, is lost to favor the latter reaction.

References

1. Review on cobaloxime: J. Halpern, B₁₂, ed. D. Dolphin, Wiley, New York, 1981, vol. 1, ch. 14; D. Dodd and M. D. Johnson, J. Organomet. Chem., 1973, 52, 1; G. N. Schrauzer, Angew. Chem., Int. Ed. Engl., 1976, 15, 417; N. B. Pahor, F. Forcolin, L. Randaccio, L. G. Marzilli, M. F. Summers and P. J. Toscano, Coord. Chem. Rev., 1985, 63, 1.
2. M. Tada, K. Inoue and K. Sugaweara, Chem. Lett., 1985, 1821; M. Tada, T. Yoshihara and K. Sugano, J. Chem. Soc., Perkin Trans. 1, 1995, 1941.
3. M. Tada, K. Inoue, K. Sugawara and M. Okabe, Chem. Lett., 1986, 703; M. Tada, T. Nakamura and M. Matsumoto, J. Am. Chem. Soc., 1988, 110, 4697.
4. S. Caddick, K. Aboutyab and R. I. West, Synlett, 1993, 231; J. Chem. Soc., Chem. Commun., 1995, 1353; S. Caddick, K. Aboutyab, K. Jenkins and R. I. West, J. Chem. Soc., Perkin Trans. 1, 1996, 675; K. Aboutyab, S. Caddick, K. Jenkins, S. Joshi and S. Khan, Tetrahedron, 1996, 52, 11329; S. Caddick, C. L. Shering and S. N. Wadman, Tetrahedron Lett., 1997, 38, 6249.
5. F. Aldabbagh and W. R. Bowman, Tetrahedron Lett., 1997, 38, 3793.
6. T. Uetake, M. Nishikawa and M. Tada, J. Chem. Soc., Perkin Trans 1, 1997, 3591.
7. M. Tada and R. Shino, J. Inorg. Biochem., 1991, 44, 89.
8. D. C. Harrowven, Tetrahedron Lett., 1993, 34, 5653.
9. L. Benati, L. Capella, P. C. Montevecchi and and P. Spagnolo, J. Org. Chem., 1994, 59, 2818; 1995, 60, 7941; L. Capella, P. C. Montevecchi and D. Nanvi, J. Org. Chem., 1994, 59, 3368; L. Capella, P. C. Montevecchi and M. L. Navacchia, J. Org. Chem., 1995, 60, 7424; P. C. Montevecchi and M. L. Navacchia, J. Org. Chem., 1998, 63, 537.
10. E. Lee, H.-S. Whang and C. K. Chung, Tetrahedron Lett., 1995, 36, 913.