Reactions of polyfluoroaromatic compounds with unusual electrophilic reagents

Abstract

Reactions of polyfluoroaromatic compounds with electrophilic reagents are interpreted on the basis of peculiarities of their electronic structure determined by introduction of fluorine in the benzene ring. The reactions of these compounds with electrophilic reagents of the type XF n +MF m − ( X = CI,Br,Xe; M = Sb, B, W ) gives the products of regiospecific addition of two fluorine atoms. The examples are given of new reactions of Friedel-Crafts type with electrophiles generated by oxidation of arsenic, mercury, lead thiocyanate, diaryldiselenides, etc., with antimony pentafluoride. These reactions were also performed for the aromatic hydrocarbons using SbF 5 in graphite. The utility of these catalysts in the synthesis of organo-elemental fluorine-containing compounds is discussed.