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Protonation and cyclization of 1,3-diarylpropynones in superacids

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Abstract

1,3-Diarylpropynones ArC≡CCOAr′ in superacids with H 0 ranging from −20 to − 14 undergo protonation at the carbonyl oxygen atoms to give stable ArC≡CC(O+H)Ar′ ions or at the acetylenic C2 atom with formation of reactive ArC+=CHCOAr′ species. The effects of the Ar and Ar′ substituents and reaction conditions on the intramolecular cyclization of ArC+=CHCOAr′ to 3-arylinden-1-ones are discussed.

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Authors and Affiliations

  1. St. Petersburg State Academy of Forestry Engineering, Institutskii per. 5, St. Petersburg, 194021, Russia

    A. V. Vasil’ev & A. P. Rudenko

  2. Universite L. Pasteur, rue B. Pascal 4, Strasbourg, 67000, France

    S. Walspurger, P. Pale, J. Sommer & M. Haouas

Authors
  1. A. V. Vasil’ev
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  2. S. Walspurger
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  3. P. Pale
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  4. J. Sommer
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  5. M. Haouas
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  6. A. P. Rudenko
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1819–1828.

Original Russian Text Copyright © 2004 by Vasil’ev, Walspurger, Pale, Sommer, Haouas, Rudenko.

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Vasil’ev, A.V., Walspurger, S., Pale, P. et al. Protonation and cyclization of 1,3-diarylpropynones in superacids. Russ J Org Chem 40, 1769–1778 (2004). https://doi.org/10.1007/s11178-005-0097-y

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  • DOI: https://doi.org/10.1007/s11178-005-0097-y

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