Polyfluoroarenes. Part XII. Some azoxy-compounds and benzotriazoles

Abstract

Polyfluoroazoxyarenes [RC₆F₄·N(O):N·C₆F₄R; R = F, p-H, or o-H] are obtained in high yield (>90%) by oxidation of the corresponding azo-compounds with trifluoroperacetic acid. Decafluoroazoxybenzene is substituted at the 2- or 4-position in the ring adjacent to the [graphic omitted]–[graphic omitted] group when treated with aqueous ethanolic ammonia, and the azoxy-compounds undergo reductive cleavage to amines and/or diamines on treatment with hydriodic acid. The reactions of azoxypolyfluoroarenes with hydrazine hydrate yield 1-anilinobenzotriazoles. Tetrafluorobenzotriazole itself may be obtained by reduction of the 1-pentafluoroanilino-compound or of tetrafluorobenzotriazol-1-ol with hydriodic acid, or by treatment of tetrafluoro-o-phenylenediamine with nitrous acid. Tetrafluorobenzotriazol-1-ol is obtained by the reaction of nitropentafluorobenzene with hydrazine hydrate.