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Kiliani-Fischer Cyanohydrin Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr359

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kiliani-Fischer Cyanohydrin Synthesis. Comprehensive Organic Name Reactions and Reagents. 359:1613–1616.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The conversion of aldose into two one-carbon-higher epimeric homologs, which involves a nucleophilic addition of cyanide to the terminal carbonyl group of an aldose, hydrolysis of cyanohydrin, and reduction of the resulting lactone is generally known as the Kiliani–Fischer cyanohydrin synthesis. The study finds that alkaline conditions are required to maintain high effective concentration of cyanide for the performance of the reaction. This reaction is useful for the preparation of higher-order aldoses and isotope-labeled carbohydrates.

Keywords:

  • D-mannose;
  • D-arabinose;
  • sodium cyanide;
  • thiazole