Nitroxide radicals. Part IX. Preparation of [2,2]paracyclophane mono- and bis-nitroxides and [2,2]paracyclophanequinones

Abstract

Two mono- and three bis-nitroxides derived from [2,2]paracyclophane have been prepared. Three hydroxy-[2,2]paracyclophanyl t-butyl hydroxylamines, formed as by-products during preparation of the bisnitroxides, have also been isolated. Two of these on oxidation yielded t-butylamino-[2,2]paracyclophanequinones by a route involving transannular oxygen migration. Spectroscopic properties of the quinones and the corresponding semiquinones have been investigated.