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Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids

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Abstract

Metal carbonate-catalyzed reactions of CH-acids (diethyl malonate, ethyl acetoacetate, ethyl cyanoacetate, and ethyl 2-acetyl- and 2-ethoxycarbonyl-5,9-dimethyldeca-4,8-dienoates) with α,β-unsaturated aldehydes (acrolein, crotonaldehyde, citral) were studied in an ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate [bmim][PF6], and in a 1-butyl-3-methylimidazolium bromide ([bmim][Br]) — benzene system. The reactions with acrolein and crotonaldehyde afforded Michael addition products, those with citral resulted in Knoevenagel addition products. Sonication increased the yields of the Michael adducts. The ionic liquid [bmim][PF6] can be recovered and repeatedly used in the reactions.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    G. V. Kryshtal, G. M. Zhdankina, I. V. Astakhova & S. G. Zlotin

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  1. G. V. Kryshtal
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  2. G. M. Zhdankina
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  3. I. V. Astakhova
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  4. S. G. Zlotin
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Kryshtal, G.V., Zhdankina, G.M., Astakhova, I.V. et al. Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids. Russian Chemical Bulletin 53, 647–651 (2004). https://doi.org/10.1023/B:RUCB.0000035651.60150.53

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