Zelinsky-Stadnikoff reaction

What is Zelinsky-Stadnikoff reaction?

The Zelinsky-Stadnikoff reaction was initially documented by Zelinsky and Stadnikoff in 1906. It is a variation of the Strecker Synthesis, wherein an aldehyde undergoes treatment with an aqueous mixture of alkali cyanide and ammonium chloride to produce the α-amino nitrile. This reaction is also referred to as the Strecker-Zelinsky-Stadnikoff cyanohydrin synthesis, Zelinsky-Stadnikoff modification, Zelinsky-Stadnikoff procedure, or Zelinsky-Stadnikoff reagent.

Zelinsky-Stadnikoff reaction - general reaction scheme - Strecker-Zelinsky-Stadnikoff cyanohydrin synthesis - Zelinsky-Stadnikoff modification - Zelinsky-Stadnikoff procedure -Zelinsky-Stadnikoff reagent
Zelinsky-Stadnikoff reaction
  • = alkyl, aryl
  • R’ = H, alkyl, aryl

Compared to the Strecker synthesis, the Zelinsky-Stadnikoff reaction is an easier method for the synthesis of α-amino nitriles and α-amino acids, with yields generally ranging from 30 to 50%.

References

Zelinsky, N. and Stadnikoff, G., Ber., 1906, 39, 1722

 

Shares