REACTION OF TRITHIAZYL TRICHLORIDE WITH ALKENES AND ALKYNES

Alkenes and alkynes react readily with trithiazyl trichloride 1 to giv e 1,2,5-thiadiazoles 2 in one step, Thus 3-amino-1,2,5-thiadiazole 5 i s now readily available from N-vinylphthalimide and 1 in two steps, Cy clic alkenes react similarly to give fused thiadiazoles (7, 12) and ph enanthrene gives the phenanthrothiadiazole 16, Tetra-substituted alken es such as 13 appear to give the analogous 3,4-dihydrothiadiazoles (e, g, 14) which spontaneously ring open to give readily hydrolysed bis(me thyleneamino) sulfides (e.g. 15), A simple set of mechanisms is propos ed for all of these reactions.