1,3-DIPOLAR CYCLOADDITIONS INDUCED BY CATION RADICALS. FORMATION OF 1,2,4-TRIAZOLES FROM OXIDATIVE ADDITION OF 1,4-DIPHENYLAZOMETHANE AND ARYL ALDEHYDE PHENYLHYDRAZONES TO NITRILES

Article abstract of DOI:10.1016/S0040-4039(01)80911-4

Reaction of thianthrene cation radical perchlorate .(1+)*ClO4(1-)> with 1,4-diphenylazomethane (DPAM) in MeCN and EtCN led to the formation of 1,2,4-triazoles.Triazole formation is attributed to oxidative cycloaddition of benzaldehyde benzylhydrazone, the tautomer of DPAM, to the solvent nitriles.In confirmation, analogous cycloadditions were achieved by reaction of Th^.(1+)*ClO4(1-) with some benzaldehyde phenylhydrazones in the same solvents.