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Oxidation with dioxiranes information


Oxidation with dioxiranes refers to the introduction of oxygen into organic molecules through the action of a dioxirane. Dioxiranes are well known for their oxidation of alkenes to epoxides; however, they are also able to oxidize other unsaturated functionality, heteroatoms, and alkane C-H bonds.[1]

  1. ^ Adam, W.; Zhao, C.-G.; Jakka, K. Org. React. 2007, 69, 1. doi:10.1002/0471264180.or069.01

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Oxidation with dioxiranes

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Oxidation with dioxiranes refers to the introduction of oxygen into organic molecules through the action of a dioxirane. Dioxiranes are well known for...

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Epoxidation with dioxiranes

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Epoxidation with dioxiranes refers to the synthesis of epoxides from alkenes using three-membered cyclic peroxides, also known as dioxiranes. Dioxiranes are three-membered...

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Dioxirane

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methyl(trifluoromethyl)dioxirane have seen some use in organic synthesis, Dioxiranes are intermediate in the Shi epoxidation reaction. Oxaziridine Ethylene oxide 1,2-Dioxetane...

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Potassium peroxymonosulfate

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corresponding acridine-N-oxide. Oxone oxidizes sulfides to sulfoxides and then to sulfones. Oxone converts ketones to dioxiranes. The synthesis of dimethyldioxirane...

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Silanol

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alternative route involves oxidation of hydrosilanes. A wide range of oxidants have been employed including air, peracids, dioxiranes, and potassium permanganate...

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Allyl group

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allylation. Allylic C-H bonds are susceptible to oxidation. One commercial application of allylic oxidation is the synthesis of nootkatone, the fragrance...

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Nitrile

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and carbon dioxide via various means of oxidative decarboxylation. Henry Drysdale Dakin discovered this oxidation in 1916. From aryl carboxylic acids (Letts...

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Shi epoxidation

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1996. Most catalyst candidates suffer from rapid decomposition/oxidation of the dioxirane intermediate and lack of electrophilicity of the reactive ketone...

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Dimethyldioxirane

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14 October 2015. Murray, Robert W. (July 1989). "Chemistry of dioxiranes. 12. Dioxiranes". Chemical Reviews. 89 (5): 1187–1201. doi:10.1021/cr00095a013...

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Oxaziridine

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and amination of carbonyls (B). Additionally, oxidation of chiral imines and oxidation of imines with chiral peracids may yield enantiopure oxaziridines...

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Aldehyde

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Swern oxidation), or amine oxides (e.g., the Ganem oxidation). Sterically-hindered nitroxyls (i.e., TEMPO) can catalyze aldehyde formation with a cheaper...

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Epoxide

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involves the oxidation of the alkene with a peroxyacid such as mCPBA. Illustrative is the epoxidation of styrene with perbenzoic acid to styrene oxide: The reaction...

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Methyldioxirane

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"Electrostatic solvent effects on the conversion of substituted carbonyl oxides to dioxiranes". Molecular Modeling Annual. 7 (4): 70–79. doi:10.1007/s008940100006...

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Acetal

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formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical...

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Dimesityldioxirane

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followed by oxidation. The synthesis had a yield of 50%. It can mainly be used as an oxidizing agent but is less oxidizing than other dioxiranes due to its...

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Organic peroxides

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biological and artificial antioxidants destroy peroxides. In fireflies, oxidation of luciferins, which is catalyzed by luciferases, yields a peroxy compound...

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Pyridine

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pyridine proceed well. Oxidation of pyridine occurs at nitrogen to give pyridine N-oxide. The oxidation can be achieved with peracids: C5H5N + RCO3H...

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Difluorodioxirane

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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...

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Thiol

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systems, an oxidizing catalyst is used to destroy the odor. A copper-based oxidation catalyst neutralizes the volatile thiols and transforms them into inert...

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Ether

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by oxidation of alkenes. The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen...

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Sulfenic acid

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clopidogrel, and prasugrel is proposed to involve sulfenic acid intermediates. Oxidation of cysteine residues in protein to the corresponding protein sulfenic...

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Nitrate

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In the NO−3 anion, the oxidation state of the central nitrogen atom is V (+5). This corresponds to the highest possible oxidation number of nitrogen. Nitrate...

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Azo compound

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0 °C. The oxidation of hydrazines (R−NH−NH−R′) also gives azo compounds. Azo dyes are also prepared by the condensation of nitroaromatics with anilines...

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Ketone

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prepared by air-oxidation of cumene. For specialized or small scale organic synthetic applications, ketones are often prepared by oxidation of secondary...

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Imine

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by the German chemist Albert Ladenburg. Usually imines refer to compounds with the general formula R2C=NR, as discussed below. In the older literature,...

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Alkene

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to determine the position of a double bond in an unknown alkene. The oxidation can be stopped at the vicinal diol rather than full cleavage of the alkene...

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Phenyl group

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possible. The phenyl group is hydrophobic. Phenyl groups tend to resist oxidation and reduction. Phenyl groups (like all aromatic compounds) have enhanced...

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Methyl group

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strongest acids.[citation needed] The oxidation of a methyl group occurs widely in nature and industry. The oxidation products derived from methyl are hydroxymethyl...

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