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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 AdditionEnolatesMichael AdditionNucleophileunsaturated CarbonylActive Methylenediketonesketo Estersketo Nitrilesnitro KetonesEnolate IonMichael DonorMichael AcceptorCarbonylCyanoNitroC C Bond Formation

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15.37 : Conjugate Addition of Enolates: Michael Addition

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15.1 : Reattività degli Enoli

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15.2 : Reattività degli ioni enolato

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15.3 : Tipi di enoli ed enolati

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15.4 : Convenzioni del Meccanismo Enolato

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15.5 : Formazione regioselettiva di enolati

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15.6 : Effetti stereochimici dell'enolizzazione

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15.7 : α-alogenazione catalizzata da acido di aldeidi e chetoni

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15.8 : α-alogenazione di aldeidi e chetoni promossa da basi

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15.9 : Alogenazione multipla di metilchetoni: reazione di aloformio

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15.10 : α-alogenazione dei derivati dell'acido carbossilico: panoramica

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15.11 : α-Bromurazione degli acidi carbossilici: reazione di Hell-Volhard-Zelinski

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15.12 : Reazioni dei composti α-alocarbonilici: sostituzione nucleofila

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15.13 : Nitrosazione degli Enoli

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15.14 : Formazione del legame C-C: Panoramica sulla condensazione aldolica

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