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amine oxide 1 An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O, an N-O bond with three additional hydrogen and/or hydrocarbon side chains attached to N. Sometimes it is written as R3NO or, wrongly, as R3N=O. 2 In the strict sense the term amine oxide applies only to oxides of tertiary amines. Sometimes it is also used for the analogous derivatives of primary and secondary amines. 3 Examples of amine oxides include pyridine N-oxide, a water-soluble crystalline solid with melting point 62-67C, and N-methylmorpholine N-oxide, which is an oxidant.

5 Pyrolytic elimination. Amine oxides, when heated to 150 to 200 C eliminate a hydroxylamine, resulting in an alkene. This pyrolytic synelimination reaction is known under the name Cope reaction. The mechanism is similar to that of the Hofmann elimination. 6 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 7 Sacrificial catalysis. Oxidants can be regenerated by reduction of Noxides, as in the case of regeneration of osmium tetroxide by Nmethylmorpholine oxide. 8 O-alkylation. Pyridine N-oxides react with alkyl halides to the Oalkylated product 9 In the Meisenheimer rearrangement (after Jakob Meisenheimer) certain N-oxides R1R2R3N+O- rearrange to hydroxylamines R2R3NO-R1 [2][3] 10 in a 1,2-rearrangement: