A Comparison of the Oxidative Reactivities of Mustard (2,2'-Dichlorodiethyl Sulfide) and Bivalent Sulfides

Abstract

Mustard (1, 2,2’-dichlorodiethyl sulfide), a liquid vesicant, can be detoxified to the crystalline sulfoxide and sulfone by oxidation, although the sulfone has been reported to still exhibit some vesicant toxicity.1,2 The sulfur in mustard is believed to be oxidatively less reactive than that in alkyl sulfides because of the presence of two large electron-withdrawing chlorine atoms. However, alkyl sulfides have often been used to simulate the oxidation of mustard.3 Recently, N-sulfonyloxaziridine derivatives such as 2 were presented as a new class of neutral organic oxidants that selectively oxidize bivalent sulfides to sulf-oxides in organic solvents4,5. © 1990, American Chemical Society. All rights reserved.