Nitroxide radicals. Part XIV. Decomposition of 1- and 2-naphthyl t-butyl nitroxides

Abstract

The spontaneous decomposition of 2-naphthyl t-butyl nitroxides yields mainly the corresponding secondary amines and 2-t-butylamino-1,4-naphthoquinones. The latter arise from intermediate 1,2-naphthoquinone t-butylimine N-oxides [formed by initial O-to-C(1) coupling of the nitroxide], which are isomerised by a process which is initiated by the nitroxide. 1-Naphthyl t-butyl nitroxide behaves in an analogous fashion, giving the corresponding secondary amine and 4-t-butylamino-1,2-naphthoquinone.