Amine Oxide - Reactions

Reactions

Pyrolytic elimination. Amine oxides, when heated to 150 to 200 °C eliminate a hydroxylamine, resulting in an alkene. This pyrolytic syn-elimination reaction is known under the name Cope reaction. The mechanism is similar to that of the Hofmann elimination.
Reduction to amines. Amine oxides are readily converted to the parent amine by common reduction reagents including lithium aluminium hydride, sodium borohydride, catalytic reduction, zinc / acetic acid, and iron / acetic acid. Pyridine N-oxides can be deoxygenated by phosphorus oxychloride
Sacrificial catalysis. Oxidants can be regenerated by reduction of N-oxides, as in the case of regeneration of osmium tetroxide by N-methylmorpholine oxide.
O-alkylation. Pyridine N-oxides react with alkyl halides to the O-alkylated product
In the Meisenheimer rearrangement (after Jakob Meisenheimer) certain N-oxides R₁R₂R₃N+O- rearrange to hydroxylamines R₂R₃N-O-R₁

in a 1,2-rearrangement:

or a 2,3-rearrangment:

In the Polonovski reaction a tertiary N-oxide is cleaved by acetic acid anhydride to the corresponding acetamide and aldehyde:

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