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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.
Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group. [1] [2]
Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of ...
TCFH (N,N,N’,N’-tetramethylchloroformamidinium hexafluorophosphate) is an electrophilic amidine reagent used to activate a number of functional groups for reaction with nucleophilies. TCFH is most commonly used to activate carboxylic acids for reaction with amines in the context of amide bond formation and peptide synthesis.
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the ...
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]
Under basic conditions, MBA reacts further with formaldehyde at the amide nitrogen to give N-hydroxymethyl,N,N′-methylenebisacrylamide.Nucleophiles such as alcohols, amines, or thiols add across the activated vinyl groups, giving mixtures of mono- and disubstituted products.
Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide: RC(O)NR' 2 + HNR" 2 → RC(O)NR" 2 + HNR' 2. The reaction is typically very slow, but it can be accelerated with Lewis acid [1] and organometallic catalysts. [2] Primary amides (RC(O)NH 2) are more amenable to this reaction.