The Journal of Organic Chemistry

Oxidative cleavage and cyclization of disulfide carboxylic acids and alcohols by aqueous iodine: a facile route to five-membered ring sultines

JT Doi, GW Luehr, WK Musker

Index: Doi, Joyce Takahashi; Luehr, Gary W.; Musker, W. Kenneth Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5716 - 5719

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Citation Number: 17

Abstract

The kinetics and mechanism of the oxidative cleavage by aqueous iodine of disullide carboxylic acids and alcohols are presented. There is evidence for intramolecular interaction of the oxygen nucleophiles. The sole product of the iodine oxidation of 3, 3'-dithiodipropanol is the sultine 1, 2-oxathiolane 2-oxide, which is formed after the rate-determining step, apparently via rapid cyclization of the sulfenyl iodide. The anchimeric assistance provided ...