Journal of Organic Chemistry p. 5346 - 5348 (1991)
Update date:2022-08-11
Topics:
Lee, Donald G.
Chen, Tao
The current literature on the oxidation of sulfides by permanganate contains a suggestion that the reaction mechanism involves an electrophilic oxygen transfer in an SN2-like mechanism.Contrary to this assumption, it is argued that the experimental facts obtained from a study of the oxidation of (arylthio)acetic acids can more reasonably be accommodated in a mechanism that is initiated by the formation of a coordinate covalent bond utilizing an unshared pair of sulfur electrons and empty manganese d-orbitals.Rearrangement of this intermediate then leads to the formation of sulfoxide and manganate(V) ion.
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