It has been suggested that this article be merged into Oxidation with dioxiranes. (Discuss) Proposed since January 2024.
Epoxidation with dioxiranes refers to the synthesis of epoxides from alkenes using three-membered cyclic peroxides, also known as dioxiranes.[1]
Dioxiranes are three-membered cyclic peroxides containing a weak oxygen-oxygen bond. Although they are able to effect oxidations of heteroatom functionality and even carbon-hydrogen bonds,[2] they are most widely used as epoxidizing agents of alkenes. Dioxiranes are electrophilic oxidants that react more quickly with electron-rich than electron-poor double bonds; however, both classes of substrates can be epoxidized within a reasonable time frame. Dioxiranes may be prepared and isolated or generated in situ from ketones and potassium peroxymonosulfate (Oxone). In situ preparations may be catalytic in ketone, and if the ketone is chiral, enantioselective epoxidation takes place. The functional group compatibility of dioxiranes is limited somewhat, as side oxidations of amines and sulfides are rapid. Nonetheless, protocols for dioxirane oxidations are entirely metal free. The most common dioxiranes employed for synthesis are dimethyl dioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFD).
Epoxidationwithdioxiranes refers to the synthesis of epoxides from alkenes using three-membered cyclic peroxides, also known as dioxiranes. Dioxiranes...
methyl(trifluoromethyl)dioxirane have seen some use in organic synthesis, Dioxiranes are intermediate in the Shi epoxidation reaction. Oxaziridine Ethylene...
Oxidation withdioxiranes refers to the introduction of oxygen into organic molecules through the action of a dioxirane. Dioxiranes are well known for...
atomes.DMD of a chiral metal catalyst followed by epoxidation, or (2) epoxidation by chiral dioxiranes, which are generated in situ from a catalytic amount...
catalytic enantioselective epoxidations, such as the Sharpless epoxidation and the Jacobsen epoxidation. Together with the Shi epoxidation, these reactions are...
The Shi epoxidation is a chemical reaction described as the asymmetric epoxidation of alkenes with oxone (potassium peroxymonosulfate) and a fructose-derived...
Oxone converts ketones to dioxiranes. The synthesis of dimethyldioxirane (DMDO) from acetone is representative. Dioxiranes are versatile oxidising agents...
14 October 2015. Murray, Robert W. (July 1989). "Chemistry of dioxiranes. 12. Dioxiranes". Chemical Reviews. 89 (5): 1187–1201. doi:10.1021/cr00095a013...
more similar to that of dioxiranes than typical oxaziridines. Notably, perfluoroalkyloxaziridines hydroxylate certain C-H bonds with high selectivity. Perfluorinated...
is a rare, stable member of the dioxirane family, known for a single oxygen-oxygen bond (O-O). Unlike most dioxiranes that decompose quickly, difluorodioxirane...
but is less oxidizing than other dioxiranes due to its stability. Difluorodioxirane Dimethyldioxirane Shi epoxidation Kirschfeld, Andreas; Muthusamy, Sengodagounder;...
organocatalytic reaction with the catalytic asymmetric epoxidation of trans- and trisubstituted olefins with chiral dioxiranes. Since that time, several...
C.; Shi, Y. (2005). "Transition State Studies on the Dioxirane-Mediated Asymmetric Epoxidation via Kinetic Resolution and Desymmetrization". J. Org....
application of alkyl hydroperoxides is without doubt the metal-catalysed epoxidation of alkenes." In the Halcon process tert-butyl hydroperoxide (TBHP) is...
fructose-derived organocatalyst used in the Shi epoxidation. The catalyst can accomplish highly enantioselective epoxidations of trans-disubstituted and trisubstituted...
infection. tert-Butyl hydroperoxide is used for epoxidation and hydroxylation reagents in conjunction with metal catalysts. Several analytical methods are...
yield epoxides: RCH=CH2 + RCO3H → RCHOCH2 + RCO2H For ethylene, the epoxidation is conducted on a very large scale industrially using oxygen in the presence...
acrylamide "is extensively metabolized, mostly by conjugation with glutathione but also by epoxidation to glycidamide (GA). Formation of GA is considered to represent...
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