Ceric ammonium nitrate mediated oxidative dimerisation of 1-methoxy naphthalene

876-878Nitration of 1-methoxy naphthalene with cerium (IV) ammonium nitrate in acetic acid gives a complex mixture of six nitro derivatives. Among the six compounds, five are known earlier and one is an unusual new dimer, 1,1′-dimethoxy-4,4′-dinitro-2,2′-binaphthyl, formed by the oxidative biradical coupling. The formation of 1,1′-dimethoxy-4,4′-dinitro-2,2′-binaphthyl is further confirmed by its reduction to 4,4′-diamino-1,1′-dimethoxy-2,2′-binaphthyl