Cyano-substituted pyrazoles transpose photo-chemically into imidazoles by two concurrent paths: (a) 1,5-interchange, probably by 2,5-bonding to a diazabicyclopentene which isomerises by nitrogen ‘walk’ before rearomatisation, and (b) 2,3-interchange, probably via an intermediate azirine; in sharp contrast, 1,5-dimethyl-3-trifluoromethylpyrazole phototransposes exclusively by the former path.
J. A. Barltrop, A. C. Day, A. G. Mack, A. Shahrisa and S. Wakamatsu, J. Chem. Soc., Chem. Commun., 1981, 604 DOI: 10.1039/C39810000604
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