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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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
26
Issue
46
Identifiers
DOI: 10.1016/s0040-4039(01)80911-4

Abstract

Abstract Reaction of thianthrene cation radical perchlorate (Th .+ClO 4 −) with 1,4-diphenylazomethane (DPAM) in MeCN and EtCN led to the formation of 1,2,4-triazoles. Triazoles 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 .+ClO 4 − with some benzaldehyde phenylhydrazones in the same solvents.

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