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Nagata Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr451

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Nagata Reaction. Comprehensive Organic Name Reactions and Reagents. 451:2007–2010.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Nagata reaction involves conjugate hydrocyanation of an α,β-unsaturated carbonyl compound from diethylaluminum cyanide or the combination of hydrogen cyanide and diethylaluminum chloride (or triethylaluminum) in an inert solvent. The study finds that ether, THF, and benzene are suitable solvents for the reaction. The study finds that diethylaluminum cyanide does not add to the simple 3-substituted cyclohex-2-enone and α-sulfinyl quinone, probably because of steric hindrance. This reaction has been further extended to the hydrocyanation of an isolated carbonyl group of β-keto sulfoxide and epoxide functionality by using Et2AlCN and hydrocyanation reagents and is found to be very useful reaction for the introduction of a cyano group into the organic compounds.

Keywords:

  • diethylaluminum cyanide;
  • trimethylsilyl cyanide;
  • β-keto sulfoxide;
  • Et2AlCN