Alkyl nitrenes from N-alkylbenzoquinone imine N-oxides

Abstract

Alkyl nitrenes have been generated by photolysis of two N-t-alkylbenzoquinone imine N-oxides. These mainly abstract hydrogen to give the corresponding amines which are trapped by reaction with benzoquinone. Intramolecular hydrogen abstraction followed by cyclisation to give a pyrrolidine is a minor process in one case.

Attempts to generate α-substituted benzyl nitrenes in this way led mainly to the production of substituted benzyl radicals by C–N bond cleavage of the N-benzylbenzoquinone imine N-oxides.