2018•Synthetic CommunicationsRequires access

Dimethyl sulfoxide/oxalyl chloride: A useful reagent for sulfenyletherification

Yang Gao, Siwei Cheng, Ting Zhang, Rui Ding, Yongguo Liu, Baoguo Sun, Hongyu Tian

Abstract

A facile method for the sulfenyletherification of unsaturated alcohols using dimethyl sulfoxide/oxalyl chloride has been described in this article. Methanesulfenyl chloride is supposed to be the compound responsible for the sulfenyletherification, which is generated by the reaction of oxalyl chloride with 2 equivalents of dimethyl sulfoxide. The formation pathway of methanesulfenyl chloride is discussed based on the formation of cyclic acetals.

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Key concepts: Oxalyl chloride, Chemistry, Dimethyl sulfoxide, Reagent, Chloride, Sulfoxide, Organic chemistry, Swern oxidation