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Baeyer-Villiger Oxidation

Baeyer-Villiger oxidation   Named Reactions in Organic Synthesis
Reaction category:
Nucleophilic substitution

Other featured reactions:

 

While exploring the ring cleavage of cyclic ketones in 1899 A. Baeyer and V. Villiger discovered that ketones could be transformed into esters and cyclic ketones into lactones or hydroxy acids by peroxyacids. This reaction became known as the Baeyer-Villiger oxidation. The oxidation of ketones by this method has several benefits:

  • It tolerates the presence of many other functional groups
  • The rearrangement steps retain the existing stereochemistry at the migrating center,
  • A wide variety of different peroxyacids can be used as oxidants.
  • The oxidation can be performed asymmetrically on racemic or prochiral ketones using enzymes or chiral transition metal catalysts.
  • A wide range of oxidizing agents can be used.
  • The activity of suitable oxidizing agents can be ranked in the following order: Trifluoroperoxyacetic acid > monopermaleic acid > monoperphthalic acid > 3,5-dinitroperbenzoic acid > p-nitroperbenzoic acid > meta chloroperoxybenzoic acid (mCPBA) > performic acid > perbenzoic acid > peracetic acid > Hydrogen peroxide and finally tert-Butyl hydroperoxide (tBuOOH).

 

Only a few methods are known for the synthesis of cage-annulated ethers. A.P Marchand and colleagues used the Baeyer-Villiger oxidation for the preparation of novel cage heterocyclic systems and developed a general process to make cage ethers from cage ketones.

Mechanism of the Baeyer-Villiger oxidation:



Baeyer-Villiger oxidation mechanism



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Other reaction categories:

Electrophilic aromatic substitution

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions NEW!



Some relevant Alfa Aesar products for the Baeyer-Villiger oxidation: Trifluoroacetic acid, 99.5+%
Trifluoroacetic acid, 99%
Trifluoroacetic acid, 99%
Hydrogen peroxide, ACS, 29-32% w/w aq. soln., stab
Hydrogen peroxide, 27% w/w aq. soln., stab
Hydrogen peroxide, 35% w/w aq. soln., stab
3-Chloroperoxybenzoic acid, 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water
tert-Butyl hydroperoxide, 70% aq. soln.

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