Canadian Journal of Chemistry

Organic sulfur mechanisms. 24. Preparation and reactions of 2-hydroxyethanesulfonyl chloride, the first hydroxyalkanesulfonyl chloride

JF King, JH Hillhouse

Index: King, James Frederick; Hillhouse, John Henry Canadian Journal of Chemistry, 1983 , vol. 61, p. 1583 - 1593

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Citation Number: 15

Abstract

2-Hydroxyethanesulfonyl chloride (1 a) is readily made by reaction of an aqueous solution of 2-mercaptoethanol (4 a) with chlorine. This is the first clearly proved preparation of a compound which is both an alcohol and a sulfonyl chloride. Reactions of 1 a with water and alcohols evidently proceed largely by intramolecular cyclization to the transient β-sultone (2 a), which then undergoes nuclcophilic ring opening to form the products. In the presence ...