Chemistry of α,β-Unsaturated Thione Dimers. 3. Reactions of Thiochalcones and 2-Arylidene-1-thiotetralones with Cumulenes Containing a Carbon-Carbon Double Bond

Article abstract of DOI:10.1021/jo01294a001

Thiochalcone, 4'-methoxythiochalcone, 2-benzylidene-1-thiotetralone, 2-(p-methoxybenzylidene)-1-thiotetralone, and 2-(p-chlorobenzylidene)-1-thiotetralone generated by the thermolysis of the corresponding thione dimer reacted as dienes with the cumulenes diphenylketene, fluorenylideneketene N-phenylimine, and tetraphenylallene.The reactions with diphenylketene and the allene gave the six-membered adduct via addition of the thione to the carbon-carbon double bond of the ketene and the allene.The reaction with the ketene imine gave two kinds of six-membered adducts: those via addition to the carbon-carbon double bond and those via addition to the carbon-nitrogen double bond.