Heteroatom Chemistry

Efficient electrophilic and nucleophilic epoxidations utilizing a sulfonylperoxy radical and peroxysulfate species

MY Park, SG Yang, YH Kim

Index: Park, Min Young; Yang, Seung Gak; Kim, Yong Hae Heteroatom Chemistry, 2002 , vol. 13, # 5 p. 431 - 436

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Abstract

Abstract Reaction of superoxide anion radical (O 2−·) with o-nitrobenzenesulfonyl chloride yields a o-nitrobenzenesulfonyl peroxy radical with strong oxidizing ability, which is capable of oxidizing aryl methylene moieties to aryl ketones and relatively electron-rich alkenes regioselectively to epoxides. The oxidizing species is tentatively attributed to the o- nitrobenzenesulfonyl peroxy radical of structure 1. Tetrabutylammonium peroxydisulfate (( ...