Journal of the Chemical Society. Chemical communications p. 604 - 606 (1981)
Update date:2022-07-31
Topics:
Barltrop, John A.
Day, A. Colin
Mack, Arthur G.
Shahrisa, Aziz
Wakamatsu, Shigeru
Cyano-substituted pyrazoles transpose photochemically 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.
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