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

G. V. Kryshtal, G. M. Zhdankina, Irina Kira Astakhova, S. G. Zlotin

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

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][PF 6], 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][PF 6] can be recovered and repeatedly used in the reactions.

OriginalsprogEngelsk
TidsskriftRussian Chemical Bulletin
Vol/bind53
Udgave nummer3
Sider (fra-til)647-651
Antal sider5
ISSN1066-5285
DOI
StatusUdgivet - mar. 2004

Fingeraftryk

2-butenal
citral
Acrolein
Ionic Liquids
Aldehydes
Acids
Sonication
Carbonates
Benzene
Metals

Citer dette

Kryshtal, G. V. ; Zhdankina, G. M. ; Astakhova, Irina Kira ; Zlotin, S. G. / Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids. I: Russian Chemical Bulletin. 2004 ; Bind 53, Nr. 3. s. 647-651.
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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][PF 6], 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][PF 6] can be recovered and repeatedly used in the reactions.",
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Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids. / Kryshtal, G. V.; Zhdankina, G. M.; Astakhova, Irina Kira; Zlotin, S. G.

I: Russian Chemical Bulletin, Bind 53, Nr. 3, 03.2004, s. 647-651.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids

AU - Kryshtal, G. V.

AU - Zhdankina, G. M.

AU - Astakhova, Irina Kira

AU - Zlotin, S. G.

PY - 2004/3

Y1 - 2004/3

N2 - 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][PF 6], 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][PF 6] can be recovered and repeatedly used in the reactions.

AB - 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][PF 6], 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][PF 6] can be recovered and repeatedly used in the reactions.

KW - α,β-unsaturated aldehydes

KW - CH-acids

KW - ionic liquids

KW - Knoevenagel reaction

KW - Michael reaction

KW - ultrasound

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DO - 10.1023/B:RUCB.0000035651.60150.53

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JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

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