Octet / Reactions
Baeyer-Villiger Oxidation
Baeyer-Villiger Oxidation (Oxidation.) Converts CC(=O)c1ccccc1 to CC(=O)Oc1ccccc1 using mCPBA, CF₃CO₃H, peracetic acid.
Oxidation
Reaction details
Name
Baeyer-Villiger Oxidation
Type
Oxidation
Starting Material
CC(=O)c1ccccc1
Product
CC(=O)Oc1ccccc1
Reagents
mCPBA
CF₃CO₃H
peracetic acid
Mechanism
- Smiles
CC(=O)c1ccccc1
- Description
Acetophenone: ketone starting material
- Smiles
CC(=O)c1ccccc1
- Description
Peracid attacks carbonyl, forms Criegee intermediate
- Smiles
CC(=O)Oc1ccccc1
- Description
Migration of more substituted group gives ester (phenyl acetate)
Tips
Ketone → Ester (oxygen inserted)
Migratory aptitude: H > 3° > 2° ≈ aryl > 1° > methyl
Aldehydes give formate esters
Cyclic ketones → Lactones
Related Reactions
epoxidation
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