Nitroxide radicals. Part 21. Spontaneous decomposition of N-aryl 1- and 2-naphthyl nitroxides

Abstract

N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines. When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced. N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.