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15.37: Conjugate Addition of Enolates: Michael Addition
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Organic Chemistry

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Conjugate Addition of Enolates: Michael Addition
 
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15.37: Conjugate Addition of Enolates: Michael Addition

The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.

Figure1

The reaction is catalyzed by a base that abstracts the acidic methylene hydrogen, generating a doubly-stabilized enolate ion that serves as the nucleophile or the Michael donor. The base employed depends on the nature and strength of the electron-withdrawing group in the nucleophile.

Figure2

The enolate attacks the β carbon of the conjugated system, which acts as the electrophile or the Michael acceptor. These molecules contain double bonds in conjugation with carbonyl, cyano, or nitro groups. Following the nucleophilic attack, a new C–C bond results in the formation of another enolate ion.

Figure3

Finally, protonation of the enolate, either by the solvent or the starting substrate, gives the Michael-addition product.

Figure4

Tags

Conjugate Addition Enolates Michael Addition Nucleophile β-carbon α,β-unsaturated Carbonyl Compound Active Methylene Compounds β-diketones β-keto Esters β-keto Nitriles α-nitro Ketones Base Catalysis Doubly-stabilized Enolate Ion Nucleophile Michael Donor Electron-withdrawing Group Electrophile Michael Acceptor Conjugated System C-C Bond Formation Enolate Ion Protonation

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