The Reaction of α-Chlorocarbenium Salts with Nitriles: Formation of Chloro-Substituted 2-Azoniaallene Salts

All articles of this category Diaryl or arylchloro substituted α-chlorocarbenium salts react with benzonitriles or dimethylcyanamide to afford chloro substituted 2-azoniaallene salts 10a, b, 11c . An X-ray structural analysis confirms the constitution of one of these salts (11c) . Substitution of the chlorine atoms in 1,3-dichloro-1,3-diphenyl-2-azoniaallene hexachloroantimonate (10a) by the nucleophiles water, p -cresol, p -toluidine, diethylamine, hydrazine, methyl-, phenyl-, 2.4,6-trichlorophenylhydrazine, hydroxylamine, N -phenylhydroxylamine, 1,3-dimethylurea, and ethyl allophanate have been carried out affording heterocycles and open-chain compounds 13-21 .