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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.
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.
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.
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.
At low pH values, it efficiently reduces aldehydes and ketones. [7] As the pH increases, the reduction rate slows and instead, the imine intermediate becomes preferential for reduction. [ 7 ] For this reason, NaBH 3 CN is an ideal reducing agent for one-pot direct reductive amination reactions that don't isolate the intermediate imine.
The Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium reagent. [1] [2] [3] The reaction was discovered by Robert H. Shapiro in 1967. [4]
The core −C(=O)−(N) of amides is called the amide group (specifically, carboxamide group). In the usual nomenclature, one adds the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH 3 CONH 2). IUPAC recommends ethanamide, but this and related formal names are rarely ...
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.