Polyperfluoroalkylthio-, sulphonyl- and selenoaromatic compounds

Abstract

A new method of the preparation of the trifluoromethylthio- and pentafluorophenylthio- or selenocopper from the reaction of the corresponding disulphides or diselenides with the copper powder in dimethylformamide or N-methylpyrrolidone is reported. ▪ Trifluoromethylthio- and pentafluoromethylthio- or selenocoppers are the convenient reactants for the preparation of the earlier unknown hexasubstituted perfluoroalkylthio- and selenobenzenes. ▪ Hexakistrifluoromethylthio- and selenobenzenes react with sodium methoxide to give products of nucleophilic substitution of trifluoromethylthio or seleno groups. These are the first examples of the anionic displacement of CF 3S or CF 3Se groups in the nucleophilic substitution reactions. 2,2′,4,4′,6,6′-Hexakis(trifluoromethylsulphonyl)diphenyl methane (I), -diphenylpropenylene (II) and -diphenylamine are synthesized. The deeply coloured salts of compounds (I) and (II) are a new type of anionic dyes.