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English: Chemical diagram showing the reduction of a generic amide to an amine using lithium aluminum hydride. Date: 19 January 2025: ... Amide reduction; Global file ...
Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group. [1] [2] Catalytic hydrogenation
In this diagram, the hydride acceptor C4 carbon is shown at the top. When the nicotinamide ring lies in the plane of the page with the carboxy-amide to the right, as shown, the hydride donor lies either "above" or "below" the plane of the page. If "above" hydride transfer is class A, if "below" hydride transfer is class B. [56]
Weinreb and Nahm originally proposed the following reaction mechanism to explain the selectivity shown in reactions of the Weinreb–Nahm amide. Their suggestion was that the tetrahedral intermediate (A below) formed as a result of nucleophilic addition by the organometallic reagent is stabilized by chelation from the methoxy group as shown. [1]
The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
In the third step, an isomerization step protonates the nitrogen atom leading to the amide. The Beckmann rearrangement mechanism. The same computation with a hydroxonium ion and 6 molecules of water has the same result, but when the migrating substituent is a phenyl group, the mechanism favors the formation of an intermediate three-membered π ...
Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones, the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3, which loses water in an elimination reaction to diazoiminium 5.
The Amadori rearrangement is an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose. [1]