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In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
Some amides can be reduced to aldehydes in the Sonn-Müller method, but most routes to aldehydes involve a well-chosen organometallic reductant. Lithium aluminum hydride reduces an excess of N,N-disubstituted amides to an aldehyde: [citation needed] R(CO)NRR' + LiAlH 4 → RCHO + HNRR' With further reduction the alcohol is obtained.
General structure of an amide (specifically, a carboxamide) Formamide, the simplest amide Asparagine (zwitterionic form), an amino acid with a side chain (highlighted) containing an amide group. In organic chemistry, an amide, [1] [2] [3] also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R ...
In organic chemistry, carbonyl reduction is the conversion of any carbonyl group, usually to an alcohol. It is a common transformation that is practiced in many ways. [ 1 ] Ketones , aldehydes , carboxylic acids , esters , amides , and acid halides - some of the most pervasive functional groups , -comprise carbonyl compounds.
Nahm and Weinreb also reported the synthesis of aldehydes by reduction of the amide with an excess of lithium aluminum hydride (see amide reduction). The Weinreb–Nahm ketone synthesis. The major advantage of this method over addition of organometallic reagents to more typical acyl compounds is that it avoids the common problem of over-addition.
The reaction mechanism involves the acylation and activation of the acid 1 to the mixed anhydride 3. The amide will serve as a nucleophile for the cyclization forming the azlactone 4. Deprotonation and acylation of the azlactone forms the key carbon-carbon bond. Subsequent ring-opening of 6 and decarboxylation give the final keto-amide product ...
An amidate/imidate anion is formed upon deprotonation of an amide or imidic acid.Since amides and imidic acids are tautomers, they form the same anion upon deprotonation.The two names are thus synonyms describing the same anion, although arguably, imidate refers to the resonance contributor on the left, while amidate refers to the resonance contributor on the right.
Illustrative is the conversion of isobutylene to tert-butylamine using HCN and sulfuric acid followed by base neutralization. The weight of the salt byproduct is greater than the weight of the amine. [12] In the laboratory, the Ritter reaction suffers from the necessity of an extremely strong acid catalyst.