Oxidation of alkylbenzenes and sulfides using peroxy intermediates

Abstract

The oxidation of various substrates having benzylic hydrogen with 2-nitrobenzene peroxysulfur intermediate generated in situ from 2-nitrobenzenesulfonyl chloride and superoxide was examined. Various alkylbenzene were readily oxidized to their ketones. In order to confirm the electrophilic radical character of 2-nitrobenzene peroxysulfur intermediate, competitive oxidations of p-substituted toluene derivatives with 2-nitrobenzene peroxysulfur intermediate were carried out (P=-1.15). In addition to, various sulfides were readily oxidized to their corresponding sulfoxides by 2-nitrobenzoyl peroxy intermediate generated in situ from 2-nitrobenzoyl chloride and superoxide. 2-nitrobenzoyl peroxy intermediate is more selective oxidizing agent than 2-nitrobenzene peroxysulfur intermediate in the oxidation of sulfides to the sulfoxides.