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Synthesis 1993; 1993(3): 263-277
DOI: 10.1055/s-1993-25843
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Synthetic Utility of Amine N-Oxides

Angelo Albini*
  • *Ist. Chimica Organica, Università, V. P. Giuria, 7, I-10125 Torino, Italy
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Publication History

Publication Date:
17 September 2002 (online)

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Tertiary amine N-oxides undergo preparatively useful reactions, namely, rearrangement to trisubstituted hydroxylamines (including 1,2-oxazaheterocycles), thermal cleavage to alkenes and hydroxylamines, addition and rearrangement reaction via iminium cation and azomethine ylide. Furthermore, these compounds are selective oxidants (inter alia for the "activation" of organometallics), and N-oxidation can be also used for protective purposes. 1. Introduction and Scope 2. Thermal Reactions 2.1. Meisenheimer Rearrangement 2.2. Cope Reaction 2.3. Other Thermal Reactions 3. Polonovski and Related Reactions 4. Other Syntheses via N-Oxides 5. Amine N-Oxides as Oxidants 5.1. Of Organic Compounds 5.2. Of Main-Group Organometallics 5.3. Of Transition-Group Organometallics 6. Other Uses