Nucleophilic replacement of methoxyl in the reaction of a sterically hindered o-benzoquinone with o-phenylenediamine

Abstract

With o-phenylenediamine, 3-t-butyl-5-methoxy-l,2-benzoquinone gives the quinone imine (VII), but only a trace of the expected phenazine (II). Dilute acid converts (VII) to the anilinophenazine (III). Chemical and spectroscopic evidence for the structures of these compounds is presented.