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Mechanism of the oxidation of organic sulphides by permanganate ion

✍ Scribed by Kalyan K. Banerji

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
494 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

The kinetics of the oxidation of number of aryl methyl, alkyl phenyl, dialkyl and diphenyl sulphides by permanganate ion to yield the sulphoxides, have been studied. The reaction is first order with respect to the sulphide and permanganate and is independent of hydrogen ion concentration. The reaction exhibited negative polar reaction constants and a small degree of steric hindrance. The lack of solvent isotope effect and the observed solvent effect ( m = 0.39 for MeSPh) are explained by an electrophilic attack of permanganate-oxygen on the sulphide yielding a polar transition state. A moderate anchimeric assistance was observed in the oxidation of o-COOMe and @.ZOOH substituted methyl phenyl sulphide. A mechanism involving a one-step electrophilic oxygen transfer from permanganate ion to the sulphide and a polar product-like transition state, has been proposed.

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