Thermolysis of thiophenedicarboxylic acid anhydrides as a route to five-membered hetarynes

MG Reinecke, JG Newsom…

Index: Reinecke, Manfred G.; Newsom, James G.; Chen, Lao-Jer Journal of the American Chemical Society, 1981 , vol. 103, # 10 p. 2760 - 2769

Full Text: HTML

Citation Number: 33

Abstract

Abstract: Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2, 3-(5) and-3, 4- dicarboxylic acid (6) and of thianaphthene-2, 3-dicarboxylic acid (7) in the presence of thiophene, 1, 3-cyclohexadiene, or benzene gave thianaphthene (Ma), presumably by aromatization of an intermediate Diels-Alder adduct of the diene traps and the aryne 2, 3- didehydrothiophene (8). A similar rationale explains the formation of dibenzothiophene ...