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Kolbe Nitrile Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr370

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kolbe Nitrile Synthesis. Comprehensive Organic Name Reactions and Reagents. 370:1661–1663.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of nitriles via SN2 substitution between an alkali metal cyanide and an alkyl halide, tosylate, or mesylate is generally referred to as the Kolbe nitrile synthesis. The study finds that the reaction performs best for primary alkylating agents in a polar aprotic solvent. It has been reported that the metal cyanide results in an isonitrile as a by-product. This reaction has been modified to use a phase-transfer catalyst and has recently been carried out in various ionic liquids. This reaction has general application in the preparation of nitriles.

Keywords:

  • SN2 substitution reaction;
  • alkylating agents;
  • phase-transfer catalyst;
  • nitriles