Standard Article

Darzens-Nenitzescu Reaction

(Nenitzescu Acylation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr181

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Darzens-Nenitzescu Reaction. Comprehensive Organic Name Reactions and Reagents. 181:851–854.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

The formation of an α,β-unsaturated ketone directly by aluminum chloride–promoted acylation of alkenes with acyl halides is known as the Darzens–Nenitzescu reaction (or Nenitzescu reductive acylation), or Nenitzescu acylation. It has been reported that under various reaction conditions, the Darzens–Nenitzescu reaction is often complicated by the formation of β-halo ketones, β,γ-enones, or β-acyloxy ketones. The aluminum chloride–promoted acylation with vinyl mercuric chloride has been found to resolve this complication, resulting in a high purity of stereochemistry. This reaction has an importance in the preparation of α,β-unsaturated ketones.

Keywords:

  • 2-butenyl methyl ketone;
  • cyclohexene;
  • β-halo ketones;
  • vinyl mercuric chloride