Carbonylation of Perfluorinated Propenylbenzenes, Indenes and 1-Alkylideneindanes in SbF Medium

Carbonylation of perfluorinated 3-arylpropenes ArCFCF=CF (Ar = CF, 3-CFCF) in the CO–SbF system at room temperature and atmospheric pressure followed by treatment of the reaction mixture with water or methanol yields (Z)-perfluoro-2-arylbut-2-enoic acids or their methyl esters, respectively. In contrast, perfluoro-2-phenylpropene does not yield carbonylation products under similar conditions. Perfluorinated 3-methyl-1H-indene, 1-methylene-, and 1-ethylideneindanes react with carbon monoxide in antimony pentafluoride medium to add two CO molecules, yielding dimethyl perfluoro-1-alkyl-1-indene-1,3-dicarboxylate as the main carbonylation product after treatment of the reaction mixture with methanol.