Skeletal transformations of perfluoroisopropyl-benzocycloalkenes under the action of SbF 5

Abstract

Cationoid skeletal rearrangements of polyfluorinated organic compounds occur rather rarely. We have studied the reactions of perfluorinated benzocyclobutenes and indanes containing the perfluoroisopropyl group in the alicyclic moiety of benzocycloalkenes with antimony pentafluoride. These compounds have been shown to undergo various skeletal transformations. The reaction may be accompanied by dealkylation, as well as by fluorination and defluorination of the products. In the absence of SbF 5 the compounds remained unchanged. Routes of the reactions involving carbocations (crypto-ions) are discussed. ▪