- Source: Amination
Amination is the process by which an amine group is introduced into an organic molecule. This type of reaction is important because organonitrogen compounds are pervasive.
Reactions
= Aminase enzymes
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Enzymes that catalyse this reaction are termed aminases. Amination can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductive amination and the Mannich reaction.
= Acid-catalysed hydroamination
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Many alkyl amines are produced industrially by the amination of alcohols using ammonia in the presence of solid acid catalysts. Illustrative is the production of tert-butylamine:
NH3 + CH2=C(CH3)2 → H2NC(CH3)3
The Ritter reaction of isobutene with hydrogen cyanide is not useful in this case because it produces too much waste.
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Usually, the amine reacts as the nucleophile with another organic compound acting as the electrophile. This sense of reactivity may be reversed for some electron-deficient amines, including oxaziridines, hydroxylamines, oximes, and other N–O substrates. When the amine is used as an electrophile, the reaction is called electrophilic amination. Electron-rich organic substrates that may be used as nucleophiles for this process include carbanions and enolates.
= Miscellaneous methods
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Alpha hydroxy acids can be converted into amino acids directly using aqueous ammonia solution, hydrogen gas and a heterogeneous metallic ruthenium catalyst.
= Metal-catalyzed hydroamination
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In hydroamination, amines add to alkenes. When substituted amines add, the result is alkene carboamination.
See also
Alkylation, the addition of an alkyl group
Acylation, the addition of an acyl group (-C(O)R)
Deamination
References
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