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

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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.

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Authors and Affiliations

  1. St. Petersburg Academy of Forestry Engineering, St. Petersburg, 194021, Russia

    A. O. Shchukin, A. V. Vasil’ev & A. P. Rudenko

  2. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhnii Novogorod, Russia

    G. K. Fukin

Authors
  1. A. O. Shchukin
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  2. A. V. Vasil’ev
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  3. G. K. Fukin
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  4. A. P. Rudenko
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Correspondence to A. O. Shchukin.

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Original Russian Text © A.O. Shchukin, A.V. Vasil’ev, G.K. Fukin, A.P. Rudenko, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 10, pp. 1455–1459.

For Communication XIV. see [1].

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Shchukin, A.O., Vasil’ev, A.V., Fukin, G.K. et al. Oxidation of aromatic compounds: XV. Oxidation of arylacetylenes in a system HF-PbO2 . Russ J Org Chem 43, 1446–1450 (2007). https://doi.org/10.1134/S1070428007100065

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  • DOI: https://doi.org/10.1134/S1070428007100065

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