Oxaziridine
| Names | |
|---|---|
| Preferred IUPAC name
Oxaziridine | |
| Systematic IUPAC name
1-Oxa-2-azacyclopropane | |
| Other names
Oxaaziridine Oxazacyclopropane | |
| Identifiers | |
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| Properties | |
| CH3NO | |
| Molar mass | 45.041 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
An oxaziridine is an organic molecule that features a three-membered heterocycle containing oxygen, nitrogen, and carbon. In their largest industrial application, oxaziridines are intermediates in the production of hydrazine. Oxaziridine derivatives are also used as specialized organic chemistry reagents for a variety of enantioselective oxidations and aminations. Oxaziridines also serve as precursors to nitrones and participate in [3+2] cycloadditions with various heterocumulenes to form substituted five-membered heterocycles.
Some oxaziridines also have the property of a high barrier to inversion of the nitrogen, allowing for the possibility of chirality at the nitrogen center.