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Thermolysis of 1,4,2-dithiazol-5-ones in the presence of dimethyl acetylenedicarboxylate yielded dimethyl isothiazole-4,5-dicarboxylates, together with sulfur, carbon oxysulfide and nitriles. The proposed mechanism involves initial expulsion of carbon oxysulfide, followed by 1,3-dipolar cycloaddition of the resulting nitrile sulfide to the alkyne. The corresponding reaction of dithiazolone 3b with ethyl propiolate afforded a ca 1:1.2 regioisomeric mixture of ethyl 3- phenylisothiazole-4- and 5-carboxylates, similar to that found for benzonitrile sulfide generated from 1,3,4-oxathiazol-2-one 1b.

Nitrile sulfides. Part 12.1,2 Generation of nitrile sulfides from 1,4,2-dithiazol-5-ones