The major crystalline products from permanganate oxidation of N-aryl-2-naphthylamines are 1,1′-coupling dimers. Structures were determined by instrumental methods and by degradation to known 7-aryldibenzo[c,g]-carbazoles. Also formed are significant quantities of carbon-nitrogen coupling products, believed to be the o-semidines. 7-Aryldibenzo[c,g]carbazoles are formed in minor amounts. No evidence was found for stable symmetrical tetraarylhydrazines.
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Bridger et al. (1968) studied this question.