A Reaction of Perfluoroalkylbenzenes with Carbon Monoxide in Antimony Pentafluoride Medium

Abstract

4-X-Perfluoroisopropylbenzenes (X = F, Cl, H, CH₃) undergo carbonylation under the action of CO/SbF₅ at room temperature and atmospheric pressure, forming 2-(4-X-tetrafluorophenyl)perfluoro-2-methylpropanoyl fluorides. Upon treatment with NH₃/CH₂Cl₂, the latter are converted into amides of the corresponding carboxylic acids and their further transformation products under the action of ammonia—4-X-2,3,5,6-tetrafluoro-1-(1,1,1,3,3,3-hexafluoropropan-2-yl)benzenes. Perfluorinated p-cymene (X = CF₃), p- and m-xylenes, as well as ethyl- and propylbenzenes, do not undergo carbonylation under the action of CO/SbF₅.