Thiophenes as traps for benzyne. 3. Diaryl sulfides and the role of dipolar intermediates

MG Reinecke, D Del Mazza…

Index: Reinecke, Manfred G.; Del Mazza, Dario; Obeng, Marcus Journal of Organic Chemistry, 2003 , vol. 68, # 1 p. 70 - 74

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Citation Number: 9

Abstract

The reactions of seven thiophenes with benzyne generated from diphenyliodonium-2- carboxylate (DPIC) under a standard set of conditions led among other products to the formation of α-and β-naphthyl phenyl sulfides 2a and 2b from thiophene (1a) and of 2c and 2d from 2-methylthiophene (1b). Dithienyl sulfides 4a-f were produced from the halothiophenes 1c-g. The structures of the naphthyl sulfides were proven by comparison ...