Carbonylation of polyfluorinated indans, tetralins and perfluoro-2,3-dihydrobenzofuran under the action of CO/SbF5

Yaroslav V. Zonov, Victor M. Karpov, Tatyana V. Mezhenkova, Vyacheslav E. Platonov

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Polyfluorinated indans and tetralins are carbonylated under the action of CO/SbF5 at room temperature and atmospheric pressure. Perfluoroindan and its 4-CF3, 5-CF3, 5-CH3, 1,1-H,H derivatives add two CO molecules to form the corresponding dimethyl indan-1,1-dicarboxylates after methanolysis, and/or 1-hydroindan-1-carboxylic acids after hydrolysis. 1-X-Perfluoroindans (X[dbnd]CF3, C2F5, C6F5, H) and 1-X-perfluorotetralins (X[dbnd]C2F5, C6F5) add one CO molecule at the 1-position to give the corresponding 1-carbonyl fluorides. Reaction of the latter with methanol gives methyl esters, whereas hydrolysis is accompanied by decarboxylation. Perfluoro-2,3-dihydrobenzofuran under the action of CO/SbF5 gives both mono- and dicarbonylation products.

Original languageEnglish
Pages (from-to)24-34
Number of pages11
JournalJournal of Fluorine Chemistry
Volume214
DOIs
Publication statusPublished - 1 Oct 2018

Keywords

  • Antimony pentafluoride
  • Carbocation
  • Carbon monoxide
  • Carbonyl fluoride
  • Carbonylation
  • Indan
  • Perfluorinated
  • Tetralin
  • DESIGN
  • IONS
  • PENTAFLUOROBENZENE
  • ALCOHOLS
  • POTENT
  • GENERATION
  • DERIVATIVES
  • PERFLUOROBENZOCYCLOALKENES
  • TRANSFORMATIONS
  • FLUORINE-CONTAINING CARBOCATIONS

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