Amine oxide



  An amine oxide, also known as amine-N-oxide and N-oxide, is a pyridine, but is sometimes also used for the analogous derivatives of primary and secondary amines.

Amine oxides are used as foam stabilizers.

Amine oxide are highly solvents.

Amine oxides are weak pH below their pKa.

Pyridine N-oxide is a crystalline solid with N-Methylmorpholine N-oxide is an oxidant.

Synthesis

Amine oxides are prepared by mCPBA in N-oxidation [1].

Reactions

  • Pyrolytic elimination. Amine oxides, when heated to 150 to 200 °C eliminate a hydroxylamine, resulting in an Hofmann elimination.
  • Reduction to amines. Amine oxides are readily converted to the parent amine by common phosphorus oxychloride
  • O-alkylation. Pyridine N-oxides react with alkyl halides to the O-alkylated product
  • In the Meisenheimer rearrangement certain N-oxides R1R2R3N+O- hydroxylamines R2R3N-O-R1 [2] [3]

Metabolites

Amine oxides are common morphine.

Amine oxides of oxygen deficient cancer tissue to the active drug.

See also

References

  1. ^ Recent trends in the chemistry of pyridine N-oxides Shaker Youssif Arkivoc 2001 Link
  2. ^ J. Meisenheimer, Ber. 52. 1667 (1919)
  3. ^ March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure Michael B. Smith, Jerry March Wiley-Interscience, 5th edition, 2001, ISBN 0-471-58589-0
 
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