Phototransposition of 2-cyanopyrroles: evidence for the intermediacy of 5-azabicyclo[2.1.0]pent-2-enes

Abstract
Irradiation of 2-cyano-N-methylpyrrole in methanol and in furan and of 2-cyanopyrrole in furan gives, in addition to the corresponding 3-cyanopyrroles, adducts whose structures, together with other experiments, indicate a transposition mechanism involving 2,5-bonding followed by ‘walk’ of the aziridine nitrogen atom.

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