Tetrahedron p. 12287 - 12298 (1997)
Update date:2022-09-26
Topics:
Baciocchi, Enrico
Lanzalunga, Osvaldo
Pirozzi, Bruno
The study of the oxidation of 4-methoxyphenethyl phenyl sulfide and 3,4-dimethoxyphenethyl phenyl sulfide with potassium 12-tungstocobalt(III)ate [Co(III)W] suggests that in the radical cations of 3,4,5-(MeO)3PhCH2SPh (4) and 2,4,6(MeO)3PhCH2SPh (5) the positive charge is not localized on the sulfur atom, but in the benzylic aromatic ring. Nevertheless, in the biomimetic and microsomal oxidation of 4 and 5 the products observed are exclusively sulfoxides and sulfones, which appears in contrast with a mechanism involving the formation of an intermediate sulfide radical cation followed by a fast oxygen rebound. A direct oxygen transfer mechanism seems most likely.
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