Thermolysis of β-hydroxysulfides bearing several heteroaromatics

Thermolyses of β-hydroxysulfides 2, bearing groups, such as 2-benzothiazolyl and 4-(4-methyl)-4H-1,2,4-triazolyl groups, were studied and found to afford the corresponding substituted styrenes 5 and hydroxy heteroaromatics in good yields, respectively. The product distribution change in the course of the thermolysis of 2a was also studied. The olefin products 5a were considered to be formed by the thermal desulfurization of the corresponding thiiranes 4a initially formed via the five-membered spiro intermediate 6a.