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Reaction of α,β-unsaturated trifluoromethyl ketones with ethyl cyanoacetate

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Abstract

β-Aryl-substituted α,β-unsaturated trifluoromethyl ketones react with ethyl cyanoacetate to give the corresponding Michael addition products, ethyl 3-aryl-2-cyano-6,6,6-trifluoro-5-oxohexanoates, which are formed as mixtures of two diastereoisomers. The reaction time and product yield depend on electron-donating properties of the substituent in the initial ketone. The reaction is not accompanied by intramolecular cyclization of the Michael adducts.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    V. G. Nenaidenko, S. V. Druzhinin & E. S. Balenkova

Authors
  1. V. G. Nenaidenko
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  2. S. V. Druzhinin
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  3. E. S. Balenkova
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Correspondence to V. G. Nenaidenko.

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Original Russian Text © V.G. Nenaidenko, S.V. Druzhinin, E.S. Balenkova, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 490–493.

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Nenaidenko, V.G., Druzhinin, S.V. & Balenkova, E.S. Reaction of α,β-unsaturated trifluoromethyl ketones with ethyl cyanoacetate. Russ J Org Chem 44, 485–488 (2008). https://doi.org/10.1134/S1070428008040027

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  • DOI: https://doi.org/10.1134/S1070428008040027

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