Abstract
Peroxymonosulfate ion, HSO, as Oxone in aqueous H2SO4, oxidizes sulfides [MeSC6H4X(p), X = Me, H, NO2] to sulfoxides and converts aryl thiobenzoates [PhCOSC6H4X(p), X = Me, H] and thiol phosphorus(V) esters [Ph2POSPh, (EtO)2POSPh, Ph2POSEt, Ph(EtO)POSEt] into the acids and sulfonate ions. Second-order rate constants increase with increasing concentration of H2SO4 (10–53 wt%), owing to the high polarity of the medium rather than to acid catalysis. The rate increases fit the Grunwald–Winstein equation based on YOTs solvent parameters derived from rate effects on SN1 solvolyses. © 1998 John Wiley & Sons, Ltd.
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