Haloketone

HALOKETONE SYNTHESIS

Haloketones and halo carbonyl compounds in general are synthesized by reaction of Carbonyl compounds with halogenation agents:

--- Halogen s, bromine and chlorine give monosubstitution, Fluorine gives polysubstitution

--- Tetrabutylammonium Tribromide

--- N-Bromosuccinimide

In the Hell-Volhard-Zelinsky Halogenation a Carboxylic Acid reacts with bromine in presence of Phosphorous Tribromide .

HALOKETONE REACTIONS

Haloketones take part in several reaction types. In reaction with a Nucleophile 2 electrophilic sites are available and in reactions with a Base several acidic protons exist due to the presence of two Electron Withdrawing Group s. The carbon halogen bond experiences increases Polarity from the Inductive Effect of the carbonyl group making the carbon atom more electropositive.

In Nucleophilic Aliphatic Substitution reactions with Potassium Iodide in Acetone , 1-chloro-2-propanone reacts faster than n-propylchloride by a factor of 36000.

In the Favorskii Rearrangement a base abstacts first an acidic α-proton and the resulting Carbanion then displaces the halogen.

The same sequence is observed in the Bingel Reaction with fullerenes

In crossed Aldol Reaction s between haloketones and Aldehyde s the initial reaction product is an Halohydrin which can subsequently form a Oxirane in the presence of base.

Haloketones are important in Heterocyclic Chemistry . An example is the use of haloketones in the Hantzsch Pyrrole Synthesis and the Hantzsch Thiazole Synthesis .

Haloketones react with phosphites in the Perkow Reaction .

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Haloketone