The fluorodechlorination of some polychloroaromatic compounds

Abstract

The aim of the research reported here was to investigate in detail the fluorodechlorination of some polychloroarenes in aprotic solvents. The particular interest of this work has been directed towards: 1) The identification of minor components in the reaction products, and 2) the isolation of intermediates by competitive and consecutive reactions and the use of such sequences preoperatively. Attempts have also been made to bring about the displacement of other groups (Meo-, p-Me-C₆H₄-SO-O-) by fluoride ion in sulpholan (tetramethylene sulphone) as methods of preparing aryl fluorides. Detailed studies have been made of the reaction of potassium fluoride with hexachlorobenzene, pentachlorobenzene, fluoropentachlorobenzene, pentachlorotoluene, pentachloroanisole, pentachlorophenyl p-toluenesulphonate, fluoro-2,3,5,6-tetrachlorobenzene, 1,2,3,4-, 1,2,3,5- and 1,2,4,5-tetrachlorobenzenes, tetrachlorophthaloyl chloride, 1,3,5-trichloro-2-nitrosobenzene, 1,3-dichloro-2-nitrosobenzene and octachloronaphthalene.