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Reactions of acetylene ketones in superacids

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Abstract

Vinyl type cations ArC+=CHCOR generated from acetylene ketones ArC≡CCOR in superacids HSO3F and CF3SO3H react with diverse benzene derivatives to form alkenylation products, E-/Z-isomers of diarylpropenone structures Ar(Ar’)C=CHCOR. The alkenylation of aromatic compounds with acetylene ketones in superacids occurs with the primary syn-addition of a hydrogen and an aryl residue to the acetylene bond followed by transformation of the product into anti-isomer under the conditions of the reaction.

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Authors and Affiliations

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

    S. A. Aristov, A. V. Vasil’ev & A. P. Rudenko

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

    G. K. Fukin

Authors
  1. S. A. Aristov
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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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Dedicated to Professor V.A.Ostrovskii on occasion of his sixtieth birthday

Original Russian Text © S.A. Aristov, A.V. Vasil’ev, G.K. Fukin, A.P. Rudenko, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 5, pp. 696–710.

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Aristov, S.A., Vasil’ev, A.V., Fukin, G.K. et al. Reactions of acetylene ketones in superacids. Russ J Org Chem 43, 691–705 (2007). https://doi.org/10.1134/S1070428007050107

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  • DOI: https://doi.org/10.1134/S1070428007050107

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