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