Collect. Czech. Chem. Commun. 1982, 47, 2711-2715

Formation of arenediazonium ion in oxidation of N,N-dimethyl-4-aminobenzene and some meta-substituted derivatives with cerium(IV) ion in acid medium

Miroslav Matrka and Jitka Pípalová

Department of Toxicology, Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


Oxidation has been studied of an experimental hepatocarcinogene N,N-dimethyl-4-aminoazobenzene and some its meta-substituted derivatives with cerium(IV) ion in 1M hydrochloric acid medium with potentiometric indication. It has been possible to prove formation of more than 50 per cent arenediazonium ion and N,N-dimethylbenzoquinonimine besides the known metabolites. Furthermore, five meta-substituted derivatives of N,N-dimethyl-4-aminoazobenzene have been studied, and the amount of the arenediazonium ion formed has been found to depend critically on character of the 3'-substituent.