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

Article abstract of DOI:10.1071/CH9951781

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 deg 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 corresponding alkenes.Second-order rate constants for these reactions are reported and implications for the metabolism of sulfur mustard are discussed.