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The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt. [1] The reaction is named after Adolf Pinner, who first described it in 1877.
The mechanism for the reduction of a nitrile to an aldehyde with DIBAL-H. The hydride reagent Diisobutylaluminium hydride, or DIBAL-H, is commonly used to convert nitriles to the aldehyde. [14] Regarding the proposed mechanism, DIBAL forms a Lewis acid-base adduct with the nitrile by formation of an N-Al bond. The hydride is then transferred to ...
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
The Ritter reaction proceeds by the electrophilic addition of either a carbenium ion or covalent species [5] [6] to the nitrile. The resulting nitrilium ion is hydrolyzed to the desired amide. Primary, [ 7 ] secondary, [ 4 ] tertiary, [ 8 ] and benzylic [ 9 ] alcohols , [ 1 ] as well as tert -butyl acetate, [ 10 ] also successfully react with ...
With nitrile electrophiles, nucleophilic addition take place by: [1] hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction.
Reaction of the nitrile with alcohol in the presence of acid gives an iminoether. Treatment of the resulting compound with ammonia then completes the conversion to the amidine. [1] Instead of using a Bronsted acid, Lewis acids such as aluminium trichloride promote the direct amination of nitriles, [2] or, in certain exceptional cases, of amides ...