The spontaneous decomposition of 2-naphthyl t-butyl nitroxides yields mainly the corresponding secondary amines and 2-t-butylamino-l,4-naphthoquinones. The latter arise from intermediate 1,2-naphthoquinone t-butylimine N-oxides [formed by initial 0-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-l,2-naphthoquinone.
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