Electrochemical reactions of fluoro-compounds. Part II. The preparation of substituted fluoro-aromatic derivatives

Abstract

2,4,5,6-Tetraflucro-1,3-phenylenediamine has been prepared by the electrochemical reduction of 1-amino-3-iminoheptafluorocyclohex-1-ene at a mercury cathode. Similarly, by reduction of other amino-imino-fluorocyclohex-1-enes and aminoheptafluorocyclohexenones, 2-trifluoromethyl-4,5,6-trifluoro-1,3-phenylenediamine, 1-amino-2,4,5,6-tetrafluorophenol, and 1-isopropylamino-2,4,5,6-tetrafluorophenol were obtained. The reduction of 1-methylamino-3-methyliminoheptafluorocyclohex-1-ene was anomalous, and gave 2,5,6-trifluoro-4H-NN′-dimethyl-1,3-phenylenediamine. 1-Amino-3-imino-pentafluorocyclopent-1-ene gave 1,3-diamino-3H-pentafluorocyclopent-1-ene without loss of fluorine. The polarographic reduction of the cyclohexene derivatives and some mono substituted heptafluorocyclohexa-1,3 and 1,4-dienes has also been investigated, and changes in E_½ discussed in terms of the Hammett σ_p function.