Pinner reaction

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The Pinner reaction (after Adolf Pinner) is an organic reaction of a nitrile with an alcohol using an acid catalyst, for instance, hydrochloric acid. The product formed is the hydrochloric acid salt of an imino ester or an alkyl imidate, which sometimes is called a Pinner salt. The reaction is a sequence of nucleophilic additions.[1][2][3][4]

These salts can react with an excess of alcohol to form the orthoester RC(OR)3, with ammonia or an amine to form an amidine or with water to form an ester.

Reaction-pinner2.png

IUPAC Nomenclature for Transformations: Alkoxy,oxo-de-nitrilo-tersubstitution, another name for this reaction is nitrile alcoholysis.

See also[edit]

References[edit]

  1. ^ A. Pinner, F. Klein (1877). "Umwandlung der Nitrile in Imide". Berichte der deutschen chemischen Gesellschaft 10 (2): 1889–1897. doi:10.1002/cber.187701002154. 
  2. ^ A. Pinner, Fr. Klein (1878). "Umwandlung der Nitrile in Imide". Berichte der deutschen chemischen Gesellschaft 11 (2): 1475–1487. doi:10.1002/cber.18780110258. 
  3. ^ A. Pinner (1883). "Ueber die Umwandlung der Nitrile in Imide". Berichte der deutschen chemischen Gesellschaft 16 (2): 1643–1655. doi:10.1002/cber.18830160235. 
  4. ^ Roger. R.; Neilson, D. G. Chem. Rev. 1961, 61, 179-211. (Review, doi:10.1021/cr60210a003)