Polyfluoroarenes. Part X. Polyfluoroaromatic azo-compounds

Abstract

Polyfluoroaromatic azo-compounds (XC₆F₄·N:N·C₆F₄X; X = F, p-H, o-H, or o-Br) are obtained by the oxidation of polyfluoro-anilines with bleaching powder or with lead tetra-acetate; the latter reagent yields fluoro-phenazines as by-products. Reduction of decafluoroazobenzene with zinc and ammonium chloride or with sodium dithionite gives decafluorohydrazobenzene, and hydriodic acid cleaves both the azo- and the hydrazo-compound to pentafluoroaniline. Reactions of decafluoroazobenzene with ammonia and with ethoxide, hydroxide, or benzenethiolate ions are described.