Metallic samarium can be used in desulfonylation in the presence of glacial acetic acid. The reaction is illustrated here for nine substrates, which include α-phenylsulfonyl cinnamonitriles, β-ketosulfones and phenylsulfonyl cycloheptane.
JuliaM., and BadetB., Bull. Chem. Soc. France, 1975, 1363 and earlier references cited therein.
2.
JuliaM., and UguenD., Bull. Chem. Soc. France, 1976, 513; T. Nakai, H. Shiono and M. Okawara, Chem. Lett., 1975, 249.
3.
KünzerH., StahnkeM., SauerG., and WiechertR., Tetrahedron Lett., 1991, 32, 1949.
4.
YanadaR., NegoroN., YanadaK., and FujitaT., Tetrahedron Lett., 1997, 38, 3271; R. Yanada, N. Negroro, K. Yanada and T. Fujita, Tetrahedron Lett., 1996, 37, 9313; M. Lautens and P.H. Delanghe, J. Org. Chem., 1995, 60, 2474; Y. Taniguchi, N. Fujii, K. Takaki and Y. Fujiwara, J. Organomet. Chem., 1995, 491. 173; T. Yamazaki, J.T. Lin, M. Takeda and T. Kitazume, Tetrahedron: Asymmetry 1990, 1, 351; G.A. Molander and J.B. Etter, J. Org. Chem., 1988, 53, 6077.
5.
BeckG., and GüntherD., Chem. Ber., 1973, 106, 2758.
6.
ManescalchiF., Synthesis, 1979, 445.
7.
SamuelssonB., and LammB., Acta. Chem. Scand., 1969, 23, 2203.
8.
MowryD.T., and MornerR. R., J. Am. Chem. Soc., 1947, 69, 1831.
