Synthetic Utility of AmineN-Oxides

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