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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Rates of Reaction of the Sulfoxides and Sulfones of Sulfur Mustard and 2-Chloroethyl Ethyl Sulfide With Hydroxide Ion in Water

RI Tilley and DR Leslie

Australian Journal of Chemistry 48(10) 1781 - 1786
Published: 1995

Abstract

The reactions of the sulfoxides and sulfones of sulfur mustard and an analogue, 2-chloroethyl ethyl sulfide, with hydroxide ion in aqueous solution at 25° have been studied. In contrast with the behaviour of the parent sulfides, for which exclusive substitution of chlorine is observed under comparable conditions, the oxidized compounds react through base-catalysed elimination of HCl to give the corresponding alkenes. Second-order rate constants for these reactions are reported and implications for the metabolism of sulfur mustard are discussed.

https://doi.org/10.1071/CH9951781

© CSIRO 1995

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