Synthesis of Tripyridiniumylpropenyl Anions from Tripyridiniumylcyclopropanes and -cyclopropenes

Article abstract of DOI:10.1021/jo00032a044

The syntheses of three stable, isolatable tripyridiniumylpropenyl anions are described. 1,2,3-Tris(4-(N-methylpyridiniumyl))propenyl anion and 1-(benzenesulfonyl)-1,2,3-tris(4-(N-methylpyridiniumyl))propenyl anion were prepared by treating the corresponding cyclopropane with a base. 1,3-Bis(benzenesulfonyl)-1,2,3-tris(4-(N-methylpyridiniumyl))propenyl anion was prepared by nucleophilic attack of benzenesulfinate anion on 3-(benzenesulfonyl)-1,2,3-tris(4-(N-methylpyridiniumyl))cyclopropene.Reduction of this cyclopropene gave either 1-(benzenesulfonyl)-1,2,3-tris(4-(N-methylpyridiniumyl))propenyl anion or hexakis(4-(N-methylpyridiniumyl))benzene depending on the solvent used.