Carbonylation of Perfluorinated Propenylbenzenes, Indenes, and 1-Alkylideneindans in Antimony Pentafluoride

Abstract

The carbonylation of perfluorinated 3-arylpropenes ArCF₂CF=CF₂ (Ar = C₆F₅, 3-CF₃C₆F₄) in SbF₅ under atmospheric CO pressure at room temperature, followed by treatment of the reaction mixture with water or methanol, afforded (Z)-perfluoro-2-arylbut-2-enoic acids or their methyl esters, respectively. In contrast, perfluoro-2-phenylpropene failed to undergo carbonylation under similar conditions. Perfluorinated 3-methyl-1H-indene and 1-methylidene- and 1-ethylideneindanes in antimony pentafluoride added two carbon monoxide molecules, and the subsequent treatment of the reaction mixture with methanol gave dimethyl perfluoro-1-alkyl-1H-indene-1,3-dicarboxylate as the major carbonylation product.