Intramolecular addition of N-nitrenes to alkenes: transition from non-concerted to concerted addition

Abstract

The nitrenes generated by oxidation of the N-amino compounds (6) and (7) are trapped competitively by the phenyl-substituted and unsubstituted double bonds: the grossly different selectivity of the nitrenes for the two double bonds in each case has been interpreted in terms of a change in mechanism from non-concerted to concerted and has allowed a description of the likely transition state geometry in the latter case.