BaeyerVilliger Oxidation: Ketones to Esters

1
Baeyer-Villiger Oxidation Ketones to Esters
Bronsted acid/base interaction Carbonyl oxygen
is protonated. This will generate a more reactive
carbonyl group
2
Baeyer-Villiger Oxidation Ketones to Esters
Nucleophilic Attack of the peroxy acid on the
highly reactive carbonyl unit
3
Baeyer-Villiger Oxidation Ketones to Esters
Sigma bonding electron-pair migrates with the
phenyl group to the electropositive oxygen
centre. This in turn initiates reorganization of
sigma- and pi-bonding electrons in the peroxy
acid group. The PHENYL group migration is very
reminiscent of the 1,2-Methyl shift in
carbocation rearrangements.
4
Baeyer-Villiger Oxidation Ketones to Esters
Positive charge on carbon is neutralized through
the loss of the hydroxyl hydrogen as a PROTON
5
Baeyer-Villiger Oxidation Ketones to Esters
Phenyl acetate