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16-September-2008 16:20:32 - Amine oxide Redirected from Nitroxide General structure of an amine oxide General structure of an amine oxide An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O- sometimes written as R3N=O or R3N→O. In the strict sense the term amine oxide applies only to oxides of tertiary amines including nitrogen-containing aromatic compounds like pyridine, but is sometimes also used for the analogous derivatives of primary and secondary amines. Amine oxides are used as protecting group for amines and as chemical intermediates. Long-chain alkyl amine oxides are used as nonionic surfactants and foam stabilizers. Amine oxide are highly polar molecules have a high polarity close to that of quaternary ammonium salts. Small amine oxides are very hydrophilic and have an excellent water solubility and a very poor solubility in most organic solvents. Amine oxides are weak bases with a pKa of around 4.5 that form R3N+-OH, cationic hydroxylamines, upon protonation at a pH below their pKa. Pyridine N-oxide is a crystalline solid with melting point 62-67°C and soluble in water N-Methylmorpholine N-oxide is an oxidant. Contents 1 Synthesis 2 Reactions 3 Metabolites 4 See also 5 External links 6 References Synthesis Amine oxides are prepared by oxidation of tertiary amines or pyridine analogs with hydrogen peroxide H2O2, Caro's acid or peracids like mCPBA in N-oxidation 1. 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 O-alkylation. Pyridine N-oxides react with alkyl halides to the O-alkylated product In the Meisenheimer rearrangement certain N-oxides R1R2R3N+O- rearrange to hydroxylamines R2R3N-O-R1 2 3 In the Polonovski reaction a tertiary N-oxide is cleaved by acetic acid anhydride to the corresponding acetamide and aldehyde 4 5: Polonovski reaction Metabolites Amine oxides are common metabolites of medication and psychoactive drugs. Examples include nicotine, Zolmitriptan, and morphine. Amine oxides of anti-cancer drugs have been developed as prodrugs that are metabolized in the oxygen deficient cancer tissue to the active drug. See also Functional group Amine, NR3 Hydroxylamine, NR2OH Sulfoxide, R2S=O Azoxy, RN=N+O-R RN=N+RO- TEMPO 2,2,6,6-Tetramethylpiperidine-1-oxyl, a stable amine oxide radical External links Chemistry of amine oxides Surfactants, types and uses pdf The amine oxides homepage Nomenclature of nitrogen compounds IUPAC definition pdf References ^ Recent trends in the chemistry of pyridine N-oxides Shaker Youssif Arkivoc 2001 Link ^ J. Meisenheimer, Ber. 52. 1667 1919 ^ March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure Michael B. Smith, Jerry March Wiley-Interscience, 5th ion, 2001, ISBN 0-471-58589-0 ^ M. Polonovski, M. Polonovski, Bull. Soc. Chim. France 41, 1190 1927. ^ Strategic Applications of Named Reactions in Organic Synthesis Paperback by Laszlo Kurti, Barbara Czako ISBN 0-12-429785-4 Retrieved from http://en..org/wiki/Amine_oxide Categories: Amine oxides | Functional groups Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages 日本語 This page was last modified on 6 April 2008, at 19:14
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