Oxidation of Tertiary Amines to Amine Oxides
Oxidation of Tertiary Amines to Amine Oxides: Mechanism
The nitrogen atom acts as nucleophile in this reaction by attacking an oxygen atom of the peroxide resulting in the formation of hydroxy ammonium ion and hydroxide anion. Subsequently, the latter reacts with the hydrogen atom of the hydroxyl group at the nitrogen releasing the amine oxide.
Tertiary amines are readily oxidized . Atmospheric oxygen is sufficient to oxidize aromatic amines to the corresponding amine oxides. Therefore, other functional groups can be oxidized only with difficulty in the presence of amines.