Canadian Journal of Chemistry

The mechanism of hydrolysis of 2-hydroxyethanesulfonyl chloride: the intermediacy of 1, 2-oxathietane 2, 2-dioxide (β-sultone)

JF King, KC Khemani

Index: King, James Frederick; Khemani, Kishan Chand Canadian Journal of Chemistry, 1989 , vol. 67, p. 2162 - 2172

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Citation Number: 13

Abstract

The hydrolysis of 2-hydroxyethanesulfonyl chloride (1) has been investigated with the aid of kinetic and product analysis studies. The results are quantitatively consistent with the mechanism of hydrolysis shown in Scheme 1, the chief features of which are (a) formation of β-sultone (2) and its rapid further reaction (the major pathway), together with (b) a minor direct hydrolysis route. The kinetics of both the β β-sultone formation and the direct ...