Russian Journal of Organic Chemistry

, Volume 43, Issue 10, pp 1446–1450 | Cite as

Oxidation of aromatic compounds: XV. Oxidation of arylacetylenes in a system HF-PbO2

  • A. O. Shchukin
  • A. V. Vasil’ev
  • G. K. Fukin
  • A. P. Rudenko
Article

Abstract

The oxidation of symmetrically substituted diarylacetylenes ArC≡CAr (Ar=C6H4R) containing strong electron-withdrawing groups R = 4-COMe, 4-CO2Me, 3-CO2Et, and 4-NO2 in a system HF-PbO2 at −10÷−20°C led within 0.5–3 h to the formation of Z,Z-1,2,3,4-tetrakis(aryl)-1,4-difluorobuta-1,3-dienes ArFC=C(Ar)−(Ar)C=CFAr. The butadiene structures obtained exist in solutions as s-cis-and s-trans-conformers and in the crystalline state are present in the stable s-cis-form.

Keywords

Diene Lead Dioxide Isomer Content Primary Cation Radical Methoxycarbonylphenyl 

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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. O. Shchukin
    • 1
  • A. V. Vasil’ev
    • 1
  • G. K. Fukin
    • 2
  • A. P. Rudenko
    • 1
  1. 1.St. Petersburg Academy of Forestry EngineeringSt. PetersburgRussia
  2. 2.Razuvaev Institute of Organometallic ChemistryRussian Academy of SciencesNizhnii NovogorodRussia

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