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Dimethyldioxirane information


Dimethyldioxirane

  Carbon, C
  Hydrogen, H
  Oxygen, O
Names
IUPAC name
3,3-Dimethyldioxirane
Other names
DMDO
Monoperoxyacetone, Murray's reagent
Identifiers
CAS Number
  • 74087-85-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 103073 checkY
PubChem CID
  • 115197
UNII
  • R5RAT196DJ checkY
CompTox Dashboard (EPA)
  • DTXSID90224990 Edit this at Wikidata
InChI
  • InChI=1S/C3H6O2/c1-3(2)4-5-3/h1-2H3 checkY
    Key: FFHWGQQFANVOHV-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O2/c1-3(2)4-5-3/h1-2H3
    Key: FFHWGQQFANVOHV-UHFFFAOYAF
SMILES
  • CC1(OO1)C
Properties
Chemical formula
C3H6O2
Molar mass 74.08 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Dimethyldioxirane (DMDO) is the organic compound with the formula (CH3)2CO2.[1][2] It is the dioxirane derived from acetone and can be considered as a monomer of acetone peroxide. It is a powerful selective oxidizing agent that finds some use in organic synthesis. It is known only in the form of a dilute solution, usually in acetone, and hence the properties of the pure material are largely unknown.[3]

  1. ^ "Robert W. Murray Biography". University of Missouri–St. Louis. Retrieved 14 October 2015.
  2. ^ Murray, Robert W. (July 1989). "Chemistry of dioxiranes. 12. Dioxiranes". Chemical Reviews. 89 (5): 1187–1201. doi:10.1021/cr00095a013.
  3. ^ Crandall, J. K.; Curc, R; D'Accolti, L; Fusco, C (15 Oct 2005). "Dimethyldioxirane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd329.pub2. ISBN 0471936235.

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Dimethyldioxirane

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Dimethyldioxirane (DMDO) is the organic compound with the formula (CH3)2CO2. It is the dioxirane derived from acetone and can be considered as a monomer...

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Thioanisole

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phenyl sulfoxide, a reaction useful for titration of oxidants such as dimethyldioxirane. Successive oxidation then leads to the sulfone. Nomenclature of Organic...

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C3H6O2

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S)-3-Methyloxiranol (S,R)-3-Methyloxiranol (S,S)-3-Methyloxiranol Dimethyldioxirane Oxetan-3-ol Oxetan-2-ol (R)-Oxetan-2-ol (S)-Oxetan-2-ol 3-Methyl-1...

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Potassium peroxymonosulfate

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sulfones. Oxone converts ketones to dioxiranes. The synthesis of dimethyldioxirane (DMDO) from acetone is representative. Dioxiranes are versatile oxidising...

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Acetone peroxide

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monomer and cyclic dimer, trimer, and tetramer forms. The monomer is dimethyldioxirane. The dimer is known as diacetone diperoxide (DADP). The trimer is...

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Methyldioxirane

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of dimethyldioxirane. Cremera, Dieter; Kraka, Elfi; G Szalay, Peter (1998). "Decomposition modes of dioxirane, methyldioxirane and dimethyldioxirane—a...

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Epoxide

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applications, other peroxide-containing reagents are employed, such as dimethyldioxirane. Depending on the mechanism of the reaction and the geometry of the...

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DMD

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DMD may refer to: Dimethyldioxirane, an organic molecule Disruptive mood dysregulation disorder Doctor of Dental Medicine, an academic degree for the...

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Cyclooctatetraene

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polyepoxides can be generated by reaction of COT with peroxy acids or with dimethyldioxirane. Various other addition reactions are also known. Furthermore, polyacetylene...

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Bleaching of wood pulp

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peroxyacetic acid, peroxyformic acid, potassium peroxymonosulfate (oxone), dimethyldioxirane, which is generated in situ from acetone and potassium peroxymonosulfate...

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Dewar benzene

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the alkenes can be epoxidized using mCPBA, peroxybenzoic acid, or dimethyldioxirane (DMDO). Using a peracid (mCPBA or peroxybenzoic acid), the epoxy product...

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Dimesityldioxirane

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oxidizing than other dioxiranes due to its stability. Difluorodioxirane Dimethyldioxirane Shi epoxidation Kirschfeld, Andreas; Muthusamy, Sengodagounder; Sander...

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Organic solar cell

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Fast and clean post-polymerization modification by oxidation using dimethyldioxirane (DMDO)". Reactive and Functional Polymers. 86: 16–26. Bibcode:2015RFPol...

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Transition metal sulfoxide complex

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Ruthenium Complexes with Dimethyldioxirane" [Oxyfunctionalization of Allyl Thioether Ruthenium Complexes with Dimethyldioxirane]. Zeitschrift für Naturforschung...

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Kinetic isotope effect

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Another example of a SKIE is the oxidation of benzyl alcohols by dimethyldioxirane where three transition states for different mechanisms were proposed...

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Difluorodioxirane

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catalysts for various organic transformations. Dimesityldioxirane Dimethyldioxirane Shi epoxidation "CAS Common Chemistry". CAS Common Chemistry. 2024-04-09...

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Coarctate reaction

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coarctate transition state is that of the epoxidation of an olefin by dimethyldioxirane. In this transition state, the oxygen atom transferred to the olefin...

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Jacobsen epoxidation

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of mixed epoxides when conjugated dienes are used as substrates. Dimethyldioxirane]] can be used as a source of O atomes.DMD of a chiral metal catalyst...

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Gambierol

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results in the active, toxic form of gambierol.Reaction conditions: (a) Dimethyldioxirane, CH2Cl2, -78 to 0 °C; DIBAL, CH2Cl2, 90% (10:1 mixture). (b) TPAP...

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Diisobutylamine

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dichlorides to give arylphosphonic amines. Diisobutylamine reacts with dimethyldioxirane to give diisobutylhydroxylamine, as typical for oxidation of secondary...

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Dioxirane

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derivative which has been characterized by X-ray crystallography. Dimethyldioxirane (DMDO) and the still more reactive methyl(trifluoromethyl)dioxirane...

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Oxidation with dioxiranes

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heteroatoms. The most common dioxiranes employed for organic synthesis are dimethyldioxirane (DMD) and trifluoromethyl-methyldioxirane (TFD). The latter is effective...

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Decomplexation

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F.; Ricart, S.; Camps, F.; Messeguer, A.; Moretó, J. M. (1992). "Dimethyldioxirane in Organometallic Chemistry. II. An Improved Procedure for the Oxidative...

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Methaneseleninic acid

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can be prepared by oxidation of selenoesters with one equivalent of dimethyldioxirane (DMDO). Use of excess DMDO affords little studied selenonic acids...

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Danishefsky Taxol total synthesis

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trimethylsilyl triflate, and a modified Rubottom oxidation using 3,3-dimethyldioxirane followed by a treatment with camphorsulfonic acid introduced a hydroxyl...

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