Dodecahydrothianthrene, a product formed by pyrolysis of a polymer from the interaction of cyclohexene sulphide and mercaptoethanol

Abstract

Cyclohexene sulphide and alkaline mercaptoethanol form 2-hydroxyethyl 2-mercaptocyclohexyl sulphide and much polymer. Pyrolysis of the polymer gives an oil containing a low yield of the trans-anti-trans isomer of dodecahydrothianthrene, whose structure has been determined. Several attempts to synthesize this new tricyclic series failed, although the bicyclic analogue, hexahydrobenzo[b]-[1,4]-dithian, was readily accessible. Water, 1,4-thioxan, 1,4-dithian, acetaldehyde, 2- methyl-1,3-oxathiolan, and 2-methyl-1,3-dithiolan have been identified amongst the pyrolysis products of thiodiglycol.