Benary reaction

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The Benary reaction is an organic reaction. In 1931 Erich Bénary [1] [2] discovered that β-(N,N-dialkylamino)-vinyl ketones reacted with Grignard reagents in a 1,4-addition to give α,β-unsaturated ketones, α,β-unsaturated aldehydes and α,β-unsaturated esters as well as poly-unsaturated ketones and aldehydes [3] after hydrolysis of the reaction intermediate and elimination of a dialkylated amine.

Organic reaction chemical reactions involving organic compounds

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions.

Nucleophilic conjugate addition

Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity, unless the alkene is activated with special substituents. With α,β-unsaturated carbonyl compounds such as cyclohexenone it can be deduced from resonance structures that the β position is an electrophilic site which can react with a nucleophile. The negative charge in these structures is stored as an alkoxide anion. Such a nucleophilic addition is called a nucleophilic conjugate addition or 1,4-nucleophilic addition. The most important active alkenes are the aforementioned conjugated carbonyls and acrylonitriles.

An enone, also called an α,β-unsaturated carbonyl, is a type of organic compound consisting of an alkene conjugated to a ketone. The simplest enone is methyl vinyl ketone (butenone) or CH2=CHCOCH3. An enal is the corresponding α,β-unsaturated aldehyde, an example being acrolein (CH2=CHCHO).

Mechanism Benary reaction.svg

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Aldol condensation type of chemical reaction

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Feist–Benary synthesis

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Reed reaction

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References

  1. Benary, Erich (1930). "Über die Einwirkung von Ammoniak und Aminen auf einige aliphatische und aromatische Oxymethylen-ketone". Berichte der deutschen chemischen Gesellschaft (A and B Series). 63 (6): 1573. doi:10.1002/cber.19300630641.
  2. Benary, Erich (1931). "Über eine Bildungsweise ungesättigter Ketone aus substituierten Amino-methylenketonen". Berichte der deutschen chemischen Gesellschaft (A and B Series). 64 (9): 2543. doi:10.1002/cber.19310640935.
  3. Näf, Ferdinand; Decorzant, René (1974). "A Stereospecific Synthesis of (E, Z)-α, β-γ, δ-Diunsaturated Aldehydes, Ketones, and Esters Using the Benary Reaction". Helvetica Chimica Acta. 57 (5): 1309. doi:10.1002/hlca.19740570507.