Lewis acid promoted reactions of n-(1-phenylcyclopropyl)alkanoyl chlorides. Ring-size effects in competitive intramolecular acylation of phenyl and cyclopropyl substituents

Doyle, Michael P.; Elliott, Robert C.; Dellaria, Joseph F.

doi:10.1021/jo00417a013

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Cited by 6 publications

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Darzens‐Nenitzescu Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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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.

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Darzens‐Nenitzescu Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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Nenitzescu Synthesis

2010

Comprehensive Organic Name Reactions and Reagents

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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.

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