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Zelinsky-Stadnikoff Reaction

(Strecker-Zelinsky-Stadnikoff Cyanohydrin Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr690

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Zelinsky-Stadnikoff Reaction. Comprehensive Organic Name Reactions and Reagents. 690:3119–3122.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The extension of the Strecker synthesis in which an aldehyde is treated with an aqueous mixture of alkali cyanide and ammonium chloride to form the α-amino nitrile is known as the Zelinsky–Stadnikoff reaction. This reaction has been compared with the Strecker synthesis. One modification of this reaction, which uses a two-phase system consisting of an aqueous solution of ammonium chloride and potassium cyanide and a water-immiscible solvent, has shown some advantages for certain aldehydes (e.g., o-nitrobenzaldehyde) without formation of tarry by-products. This reaction is useful for the preparation of α-amino nitriles as well as α-amino acids.

Keywords:

  • α-amino nitrile;
  • aldehydes;
  • ammonium hydroxide;
  • alkali cyanide