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Wohl-Ziegler Bromination

Wohl-Ziegler bromination   Named Reactions in Organic Synthesis

Reaction category:
Radical reactions!

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In 1919, German chemist Alfred Wohl investigated the reaction between 2,3-dimethyl-2-butene and N-bromoacetamide in diethyl ether and discovered that the double bond of the substrate remained unchanged and one of the methyl groups was replaced by bromine. This discovery was interesting, as the reaction was previously thought to require the use of bromine at high temperatures to react with the alkenes. In 1942, Karl Ziegler carried out a comprehensive study of the utility of N-bromosuccinimide (NBS) in the allylic bromination of olefins and demonstrated the synthetic value of the process. Subsequently, the addition of bromine at the allylic position of olefins or at the benzylic position of alkylated aromatic or heteroaromatic compounds became known as the Wohl?Ziegler bromination.

NBS is the commercially available reagent that is by far the most effective, giving the least amount of side products. In the past, benzene and carbon tetrachloride were used as solvents, however safety and environmental concerns have led to the use of ionic liquids or even solvent-free systems. Typically the reaction is carried out in the presence of a radical initiator such as AIBN or dibenzoyl peroxide.

The Wohl?Ziegler bromination has been utilised in several total synthesis campaigns including James M. Cook’s preparation of (-)-tryprostatin A, a natural product isolated from a marine fungus that inhibits cell cycle progression.

Mechanism of the Wohl-Ziegler bromination

Reaction mechanism of the Wohl-Ziegler bromination


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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions

Rearrangement reactions

Electrophilic addition reactions


Some relevant Alfa Aesar products for the Wohl-Ziegler bromination:

N-Bromosuccinimide, 99%
Dibenzoyl peroxide, 97% (dry wt.), wet with 25% water



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