Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
A generic oxaziridine derivative.
An oxaziridine is an organic molecule that features a three-membered heterocycle containing oxygen, nitrogen, and carbon. In their largest application, oxaziridines are intermediates in the industrial production of hydrazine. Oxaziridine derivatives are also used as specialized reagents in organic chemistry for a variety of oxidations, including alpha hydroxylation of enolates, epoxidation and aziridination of olefins, and other heteroatom transfer reactions. Oxaziridines also serve as precursors to nitrones and participate in [3+2] cycloadditions with various heterocumulenes to form substituted five-membered heterocycles. Chiral oxaziridine derivatives effect asymmetric oxygen transfer to prochiral enolates as well as other substrates. 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.
^"CID 15817734 - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
An oxaziridine is an organic molecule that features a three-membered heterocycle containing oxygen, nitrogen, and carbon. In their largest application...
Davis reagent (3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine or 2-(benzenesulfonyl)-3-phenyloxaziridine) is a reagent used for oxidation in the Davis oxidation...
the active dioxirane form before proceeding in the catalytic cycle. Oxaziridines such as chiral N-sulfonyloxaziridines effect enantioselective ketone...
deficient oxygen of the oxaziridine ring. This reaction type is extended to asymmetric synthesis by the use of chiral oxaziridines derived from camphor (camphorsulfonyl...
H2O Oxidation of the imine to the oxaziridine: Me(Et)C=NH + H2O2 → Me(Et)CONH + H2O Condensation of the oxaziridine with a second molecule of ammonia...
to: Formaldoxime Formamide, or methanamide Nitrosomethane [Wikidata] Oxaziridine This set index page lists chemical structure articles associated with...
hydrogen peroxide to the oxaziridine, a three-membered ring containing carbon, oxygen, and nitrogen. Next, the oxaziridine gives the hydrazone by treatment...
reactions are useful for the enantioselective synthesis of chiral epoxides. Oxaziridine reagents may also be used to generate epoxides from alkenes. Arene oxides...
sulfoxides or sulfones, disulfides or thiols to sulfonyl halides, imines to oxaziridines. It can also de-aromatize phenols. Heterogeneous reactions of sodium...
reactivity may be reversed for some electron-deficient amines, including oxaziridines, hydroxylamines, oximes, and other N–O substrates. When the amine is...
for alpha-hydroxylation via enol or enolate structures include Davis oxaziridine, oxygen, and various peroxyacids (see Rubottom oxidation). This reagent...
Imine are oxidized with meta-chloroperoxybenzoic acid (mCPBA) to give an oxaziridines. Imines are intermediates in the alkylation of amines with formic acid...
tert-Butyl hydroperoxide or, more efficiently, (1S)-(+)-(10-camphorsulfonyl)-oxaziridine (CSO). The step of oxidation may be substituted with a sulfurization...
(10). Oxidation of the enolate of ketone 10 with (-)-camphorsulfonyl oxaziridine (11) gave α-hydroxyketone 12. Reduction of the ketone group with 20 equivalents...
synthesis, Dioxiranes are intermediate in the Shi epoxidation reaction. Oxaziridine Ethylene oxide 1,2-Dioxetane 1,3-Dioxetane Lovas, F.J.; Suenram, R.D...
organic oxidation with an electrophilic source of oxygen such as an oxaziridine or mCPBA. In the Saegusa–Ito oxidation, certain silyl enol ethers are...
with peracids (such as cyclic sulfonimines as precursors of reactive oxaziridines) or sugar-based ketones that form bleach-active dioxiranes with hydrogen...
catalyst. The acyloin group in 13 was introduced by KHMDS and Davis’ oxaziridine (see Holton Taxol total synthesis for another use of this system) and...
for oxidations of electron-poor double bonds, and sulfonyl-substituted oxaziridines are effective for electron-rich double bonds. Metal-based oxidants are...
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