Oxidation of a variety of substituted dihydrotetraazanaphthalene derivatives (I-IV) with 2, 3-dichloro-5, 6-dicyanoquinone afforded corresponding dehydrogenated aromatic deriva tives (V, VII, IX, and X). However, oxidation with potassium ferricyanide, bromine or nitrobenzene gave rise to oxidative elimination of the substituent in addition to normal dehydrogenation, depending upon the variety of the substituent. The substi-tuents readily removed by this novel C-C bond cleavage were benzyl, allyl, tert-butyl, cyclohexyl and α-hydroxyalkyl groups.
