Kinetics and Mechanism of the Oxidation of Organic Sulfides by N-Bromobenzamide

Article abstract of DOI:10.1021/jo00306a017

Kinetics of oxidation of 34 organic sulfides by N-bromobenzamide (NBB), to yield the corresponding sulfoxides, have been studied.The reaction is first-order with respect to the sulfide, NBB, and hydrogen ions.There is no effect of added benzamide.Protonated NBB has been postulated as the reactive oxidizing species.Reactivity of the sulfides toward NBB was subjected to correlation analysis by using multiparametric equations.The polar reaction constants are negative.Steric effects play a minor inhibitory role.A mechanism involving formation of a halogenosulfonium cation, in the rate-determining step, has been proposed.