Articles written in Journal of Chemical Sciences
Volume 97 Issue 5-6 December 1986 pp 555-563 Organic
Detailed kinetic investigations of the oxidation of methyl phenyl sulphoxide and diphenyl sulphoxide by peroxomonosulphate in aqueous acetic acid medium reveal that the reactions are first-order, both in the sulphoxide and in the oxidant. Studies with substituted phenyl methyl sulphoxides and 4,4′-disubstituted diphenyl sulphoxides show that electron-releasing groups accelerate the rate of oxidation and electron-withdrawing groups retard it. A fair correlation between log k2 and Hammett substituent constants has been observed in the two series. The mechanism proposed involves the rate-determining nucleophilic attack of the sulphoxide sulphur at the outer terminal peroxo oxygen atom of HSO5−.
Volume 103 Issue 5 October 1991 pp 637-643 Organic
The oxidation of 4,4′-disubstituted diphenyl sulphoxides by potassium permanganate on Hammett type correlations give a small positive ρ value (0.34). This is in contrast to the oxidation of aryl methyl sulphides (ρ = −1.36) by the permanganate ion. On the basis of rate data a mechanism of nucleophilic attack of MnO4− on the substrate has been proposed.
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