Simultaneous 1,2-, 1,3- and 1,4-addition of trithiazyl trichloride to a conjugated diene

Abstract

1,4-Diphenylbuta-1,3-diene and trithiazyl trichloride 1 react to give a bi(thiadiazole) 2, an isothiazoloisothiazole 3, a dithiazolothiazine 4 and the thiazinodithiatriazepines 5 and 6, all of which could arise from initial addition of the trimer 1, or its monomer, to the conjugated diene by 1,2-,1,4- and, for the first time to an all-carbon diene, 1,3-(‘criss-cross’) cycloaddition reactions.