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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 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 nitriles in the presence of strong acids to form amides via the Ritter reaction. A wide range of nitriles can be used.
The conversion of a general nitrile to either an amide or carboxylic acid is facilitated by nitrilase. [5] [1] Below is a list of steps involved in transforming a generic nitrile compound with nitrilase: [4] The electrophilic carbon of the nitrile is subject to nucleophilic attack by one of the two SH groups on nitrilase.
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 ...
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.
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 arene with isocyanate catalysed by aluminium trichloride, formation of aromatic amide. Ritter reaction [28] Alkenes, alcohols, or other carbonium ion sources Secondary amides via an addition reaction between a nitrile and a carbonium ion in the presence of concentrated acids. Photolytic addition of formamide to olefins [29] Terminal ...
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 ...