Synthesis and structure of the dithienostannole anion

Novel dithienostannoles were synthesized by the reactions of the corresponding dilithiobithiophenes with dichlorodiphenylstannane. A unique byproduct, 10-membered ring compound was also obtained. Reduction of type A dithienostannole with lithium afforded 2,2′-dilithio-3,3′-bithiophene, while reduction of type B dithienostannole with lithium afforded the corresponding dithienostannole anion. The structure and aromaticity of the dithienostannole anion are also discussed.