Oxidation of furans with dimethyldioxirane

Adger, B. M.; Barrett, C. B.; Brennan, J.; McKervey, M. Anthony; Murray, Robert W.

doi:10.1039/c39910001553

Cited by 84 publications

(58 citation statements)

References 7 publications

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“…A similar mechanism has been proposed for the oxidation of furan and alkyl-substituted furans with other oxidising agents such as peracids [11] and dioxiranes. [12] Since water is present in the TS-1/H 2 O 2 system, the initially formed dialdehydes are converted to the corresponding hydrates.…”

Section: Oxidation Of Furan and Alkyl-substituted Furansmentioning

confidence: 99%

Titanium Silicalite 1 (TS‐1) Catalyzed Oxidative Transformations of Furan Derivatives with Hydrogen Peroxide

et al. 2004

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The oxidation of furan derivatives with titanium silicalite 1 (TS-1) and hydrogen peroxide is described. Oxidation products are identified and possible reaction pathways are discussed. It is shown that the oxidation of these compounds occurs via epoxidation of one of the furan double bonds. The initially formed epoxides immediately undergo rearrangement, furans yielding unsaturated 1,4-dicarbonyl compounds and furfuryl alcohols yielding 6-hydroxy-2H-pyran-3(6H)-ones. The latter compounds originate from cyclization of intermediate enedione alcohols. The presented method is particularly useful for the oxidation of 2,5-dimethylfuran to 3-hexene-2,5-dione and the conversion of furfuryl alcohol to 6-hydroxy-2H-pyran-3(6H)-one, a versatile synthon in organic synthesis.

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Section: Oxidation Of Furan and Alkyl-substituted Furansmentioning

confidence: 99%

Titanium Silicalite 1 (TS‐1) Catalyzed Oxidative Transformations of Furan Derivatives with Hydrogen Peroxide

et al. 2004

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“…[21] Finally,t og ain insighti nto the mechanism of the described transformation,w ee valuated two possible pathways to the phthaloylhydrazones( Scheme 9). The proposed mechanism includes aziridination of the heterocycle followed by the rearrangemento fu nstable fused aziridine of type A.A tt he same time, an easy oxidation of furan by treatment with meta-chloroperoxybenzoic acid (m-CPBA), [23] Pb(OAc) 4 , [24] dimethyldioxirane, [25] or titaniums ilicalite 1/H 2 O 2 [26] is known to lead to a1 ,4-dicarbonyl species. For example, (Z)-1,2-diaroylethenes were obtained from 2,5-diarylfurans by using the same oxidant (Pb(OAc) 4 )a si no ur work.…”

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confidence: 99%

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

2016

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The oxidative addition of N-aminophthalimide to substituted2-vinylfurans provides monophthaloylhydrazones of (2Z)-hexa-2,5-diene-1,4-dione derivativesi nstead of 2-furylaziridines by proceeding through an aziridination of the endocyclic furan C=Cb ond followed by ar egio-and stereoselective rearrangement of the bicyclic intermediate. The formation of stable aziridines can then occur through the aziridination of the (E)-C=Cb ondo ft hese phthaloylhydrazones. Detailed structure elucidations and mechanistic considerations are provided.

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“…Oxidation of 2-methylfuran gave Z-4-oxo-2-pentenal in good yield using either dimethyl dioxirane in acetone or m-chloroperbenzoic acid as the oxidant (Adger et al, 1991). Hex-3-ene-2,5-dione was obtained in the same way from 2,5-dimethylfuran as a mixture of the E-and Z-isomers (2:3) in excellent yield (Adger et al, 1991). Any further attempts at purification increased the proportion of the E-isomer.…”

Section: Synthesis Of Commercially Unavailable Chemicalsmentioning

confidence: 99%

Measurements of photo-oxidation products from the reaction of a series of alkyl-benzenes with hydroxyl radicals during EXACT using comprehensive gas chromatography

et al. 2003

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Abstract. Photo-oxidation products from the reaction of a series of alkyl-benzenes, (benzene, toluene, p-xylene and 1,3,5-trimethyl-benzene) with hydroxyl radicals in the presence of NO x have been investigated using comprehensive gas chromatography (GC×GC). A GC×GC system has been developed which utilises valve modulation and independent separations as a function of both volatility and polarity. A number of carbonyl-type compounds were identified during a series of reactions carried out at the European Photoreactor (EUPHORE), a large volume outdoor reaction chamber in Valencia, Spain. Experiments were carried as part of the EXACT project (Effects of the oXidation of Aromatic Compounds in the Troposphere). Two litre chamber air samples were cryo-focused, with a sampling frequency of 30 minutes, allowing the evolution of species to be followed over oxidation periods of 3-6 hours. To facilitate product identification, several carbonyl compounds, which were possible products of the photo-oxidation, were synthesised and used as reference standards.For toluene reactions, observed oxygenated intermediates found included the co-eluting pair α-angelicalactone/4-oxo-2-pentenal, maleic anhydride, citraconic anhydride, benzaldehyde and p-methyl benzoquinone. In the p-xylene experiment, the products identified were E/Z-hex-3-en-2,5-dione and citraconic anhydride. For 1,3,5-TMB reactions, the products identified were 3,5-dimethylbenzaldehyde, 3,5-dimethyl-3H-furan-2-one and 3-methyl-5-methylene-5H-furan-2-one. Preliminary quantification was carried out on identified compounds using liquid standards. Comparison of FTIR and GC×GC for the measurement of the parent aroCorrespondence to: J. F. Hamilton (jacquih@chemistry.leeds.ac.uk) matics generally showed good agreement. Comparison of the concentrations observed by GC×GC to concentrationtime profiles simulated using the Master Chemical Mechanism, MCMv3, demonstrates that this mechanism significantly over-predicts the concentrations of many product compounds and highlights the uncertainties which exist in our understanding of the atmospheric oxidation of aromatics.

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Oxidation of furans with dimethyldioxirane

Abstract: Dimethyldioxirane reacts rapidly at room temperature in acetone with a variety of furans, furnishing in high yield products of oxidative ring opening and, with 2-furanmethanol, 2H-pyran-3(6H)-one via subsequent ring closure.

Cited by 84 publications

References 7 publications

Titanium Silicalite 1 (TS‐1) Catalyzed Oxidative Transformations of Furan Derivatives with Hydrogen Peroxide

Titanium Silicalite 1 (TS‐1) Catalyzed Oxidative Transformations of Furan Derivatives with Hydrogen Peroxide

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

Measurements of photo-oxidation products from the reaction of a series of alkyl-benzenes with hydroxyl radicals during EXACT using comprehensive gas chromatography

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