Haloalkylation reaction of polyfluoroaromatic amino, hydroxy and thio derivatives with ArCCl 3 or ArCF 3in the presence of AlCl 3. Synthesis of polyfluoroaromatic compounds of various classes.

Abstract

A general haloalkylation reaction of polyfluoroaromatic amino, hydroxy and thio derivatives with compounds of the formula ArCCl 3 or ArCF 3 in the presence of AlCl 3 has been found. The reaction proceeds at heteroatom and leads to compounds of various classes. The products of the reactions of polyfluoroaromatic amines and AlCl 3 with benzotrichlorides or benzotrifluorides have been shown to be polyfluoroaromatic imidoyl chlorides. For compound containing several CF 3 or CCl 3 groups in a molecule only one trihalomethyl group is involved in formation of the imidoyl chloride group. Polyfluorinated phenols react with benzotrichlorides and benzotrifluorides in the presence of AlCl 3 to give polyfluorophenol esters of the respective carboxylic acids. The haloalkylation reaction of polyfluorinated thiophenols with CCl 4/AlCl 3 leads to bis(arylthio)dichloromethanes. With benzotrichlorides or benzotrifluorides bis(arylthio)arylchloromethanes are formed. ▪ Peculiarities of these processes are discussed as well as routes of transformations.