The Journal of Organic Chemistry

Oxidation of N-acyl-, N-sulfonyl-, and N-arylsulfilimines to sulfoximines by m-chloroperoxybenzoate anion

SL Huang, D Swern

Index: Huang,S.; Swern,D. Journal of Organic Chemistry, 1979 , vol. 44, p. 2510 - 2513

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Citation Number: 31

Abstract

N-Acyl-, N-sulfonyl-, and N-arylsulfilimines are rapidly oxidized to the corresponding sulfoximines in high to virtually quantitative yields by m-chloroperoxybenzoate anion generated in situ in basic aqueous alcoholic media. In the one N-aryl case studied, S, S- dimethyl-N-(pnitropheny1) sulfilimine is converted unexpectedly to p-nitrosonitrobenzene in excellent yield by m-chloroperoxybenzoic acid but if the m-chloroperoxybenzoate anion is ...