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Reaction of 5-phenylpenta-2,4-dienoic acid with benzene in trifluoromethanesulfonic acid

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Abstract

The reaction of 5-phenylpenta-2,4-dienoic acid with benzene in CF3SO3H, depending on the reaction conditions, gives three products, namely, 5,5-diphenylpent-2-enoic acid and tetralone and indanone derivatives. These carbocyclic compounds are formed through the addition of two benzene molecules to the starting diene acid and subsequent intramolecular acylation.

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Authors and Affiliations

  1. St. Petersburg State Forest Technical University, 5 Institutskiy per., 194021, St. Petersburg, Russian Federation

    A. R. Ismagilova, D. N. Zakusilo & A. V. Vasilyev

  2. Research Institute of Synthetic Rubber, 1 Gapsal’skaya ul., 198035, St.-Petersburg, Russian Federation

    L. V. Osetrova

  3. Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., 199034, St. Petersburg, Russian Federation

    A. V. Vasilyev

Authors
  1. A. R. Ismagilova
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  2. D. N. Zakusilo
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  3. L. V. Osetrova
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  4. A. V. Vasilyev
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Corresponding author

Correspondence to A. V. Vasilyev.

Additional information

Russian Chemical Bulletin, International Edition, Vol. 69, No. 10, pp. 1928–1932, October, 2020

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1928–1932, October, 2020.

This work was financially supported by the Russian Science Foundation (Project No. 18-13-00008 “Conjugated unsaturated structures (enynes, dienes, diynes, allenes, etc.) as sources of multisite electrophiles in the synthesis of biologically active compounds”).

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Ismagilova, A.R., Zakusilo, D.N., Osetrova, L.V. et al. Reaction of 5-phenylpenta-2,4-dienoic acid with benzene in trifluoromethanesulfonic acid. Russ Chem Bull 69, 1928–1932 (2020). https://doi.org/10.1007/s11172-020-2980-7

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  • DOI: https://doi.org/10.1007/s11172-020-2980-7

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