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Nenitzescu Synthesis

(Darzens-Nenitzescu Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr458

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Nenitzescu Synthesis. Comprehensive Organic Name Reactions and Reagents. 458:2038–2041.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The formation of an α,β-unsaturated ketone directly by aluminum chloride-promoted acylation of alkenes with acyl halides is generally referred to as the Nenitzescu synthesis. The study finds the formation of the saturated ketones is probably caused by the intermolecular hydrogen transfer from the solvent. It has been observed that under various reaction conditions, the Nenitzescu synthesis is often complicated with the formation of β-halo ketones, β,γ-enones, or β-acyloxy ketones and this complication can be overcome by an aluminum chloride-promoted acylation with vinyl mercuric chloride. This reaction is useful in the preparation of α,β-unsaturated ketones.

Keywords:

  • 4-phenyl cyclohexyl methyl ketone;
  • cyclohexene;
  • β-halo ketones;
  • vinyl mercuric chloride