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Abstract <p>The carbonylation of perfluorinated 3-arylpropenes ArCF<sub>2</sub>CF=CF<sub>2</sub> (Ar = C<sub>6</sub>F<sub>5</sub>, 3-CF<sub>3</sub>C<sub>6</sub>F<sub>4</sub>) in SbF<sub>5</sub> under atmospheric CO pressure at room temperature, followed by treatment of the reaction mixture with water or methanol, afforded (<i>Z</i>)-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-1<i>H</i>-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-1<i>H</i>-indene-1,3-dicarboxylate as the major carbonylation product.</p>

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

  • 期刊论文

  • 发表日期：

    2025年7月1日

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  • Ya. V. Zonov,
  • V. M. Karpov,
  • T. V. Mezhenkova

摘要

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.