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Knoevenagel condensation : ウィキペディア英語版
Knoevenagel condensation

The Knoevenagel condensation reaction is an organic reaction named after Emil Knoevenagel. It is a modification of the aldol condensation.〔Jones, G. ''Org. React.'' 1967, ''15''.〕
A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated (hence ''condensation''). The product is often an alpha, beta conjugated enone.
In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the form
* Z–CH2-Z or Z–CHR–Z for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid.
* Z–CHR1R2 for instance nitromethane.
where Z is an electron withdrawing functional group. Z must be powerful enough to facilitate deprotonation to the enolate ion even with a mild base. Using a strong base in this reaction would induce self-condensation of the aldehyde or ketone.
The Hantzsch pyridine synthesis, the Gewald reaction and the Feist–Benary furan synthesis all contain a Knoevenagel reaction step. The reaction also led to the discovery of CS gas.
==Doebner modification==

With malonic compounds the reaction product can lose a molecule of carbon dioxide in a subsequent step. In the so-called Doebner modification the base is pyridine. For example, the reaction product of acrolein and malonic acid in pyridine is ''trans-2,4-Pentadienoic acid'' with one carboxylic acid group and not two.

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