Dioxiranes. 20. Preparation and properties of some new dioxiranes

Murray, Robert W.; Singh, Munendra; Jeyaraman, R.

doi:10.1021/ja00030a032

Cited by 69 publications

(34 citation statements)

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“…A number of ketones gave no products of oxidation at all (see Table 1). Since some of the dioxiranes formed from these ketones have in fact been described (23), the tentative conclusion is that these dioxiranes are more disposed to radical fragmentation (16). Epoxidation of natural triglycerides.…”

Section: I-mentioning

confidence: 99%

Reactions of dioxiranes with selected oleochemicals

Sonnet

Lankin

McNeill

1995

J Americ Oil Chem Soc

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ABSTRACI: Reaction of fatty acids with dimethyldioxirane in acetone produces ketoacids in 9-12% yields in which the ketone carbonyl is distributed along the fatty chain. The n-1 position appears to be preferred. Lactones of hydroxy fatty acids are oxidized by this reagent, but in low yields, to the corresponding ketoacids. Biphasic epoxidations with methylethyldioxirane in 2-butanone were conducted with methyl o[eate and methyl ricinoleate to give the corresponding epoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.

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Section: I-mentioning

confidence: 99%

Reactions of dioxiranes with selected oleochemicals

Sonnet

Lankin

McNeill

1995

J Americ Oil Chem Soc

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“…In 1992, Murray et al. also developed the salting out extraction method to isolate some further isolated dioxirane from less volatile ketones (e.g., cyclohexanone dioxirane in solution of the parent ketone) . The synthesis, isolation, and spectroscopic characterization of the methyl(trifluoromethyl)‐dioxirane (TFDO, 1 b ) from 1,1,1‐trifluoropropanone (TFP) and oxone was successfully reported for the first time by Curci's group at the University of Bari in 1988 .…”

Section: Introductionmentioning

confidence: 99%

Continued Progress towards Efficient Functionalization of Natural and Non‐natural Targets under Mild Conditions: Oxygenation by C−H Bond Activation with Dioxirane

D’Accolti

Annese

Fusco

2019

Chemistry A European J

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The successful isolation and characterization of a dioxirane species in 1988 opened up one of the most attractive methods for the efficient oxidation of simple and/or structurally complex molecules. Dioxirane today rank among the most powerful tools in organic chemistry, with numerous applications in commercially important processes. They were quickly recognized as efficient oxygen transfer agents, especially for epoxidations and for a wide range of O‐insertion reactions into C−H bonds. Dioxirane possess catalytic activity and appear as highly (chemo‐, regio‐, and stereo‐) selective oxidants, despite their reactivity under mild and strictly neutral conditions being controlled by a combination of steric and electronic factors. In this review, we discuss some of the most recent and significant developments in the selective homogeneous and heterogeneous oxyfunctionalization of non‐activated C−H bonds in hydrocarbons of natural and non‐natural targets by using isolated dioxirane or, more generally, by using the ketones (i.e., the dioxirane precursors) as organocatalysts.

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“…Dioxiranes can be used either generated in situ or as isolated species. The procedure for the isolation of dioxiranes is rather cumbersome, [23,24] which limits their practical use. The use of dioxiranes generated in situ is more convenient.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of partially norbornylized linseed oil

Chen

Soucek

Simonsick

et al. 2002

Macromol. Chem. Phys.

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Epoxidation of linseed oil was performed with peracetic acid formed in situ by the reaction of hydrogen peroxide and acetic acid in the presence of Amberlite 120H as catalyst, and toluene as solvent. Some variables were evaluated as temperature and the molar ratio and solution of aqueous hydrogen peroxide (30 and 50 wt%) for obtaining a maximum of yield and conversion of epoxidized oil. The characterization of conversion of double bonds (DB) to epoxy ring, the relative percentage of epoxidation and selectivity, were performed by 1 H-NMR and FTIR-HART. The conditions rendered a maximum epoxidation of 93.4%, a conversion or double bonds of 97% and a selectivity of 96.3% were obtained at 80°C, employing a molar ratio 1:1.5 of double bonds (DB) to H 2 O 2 (50 wt%), 1:0.5 of DB to acetic acid, and 25 wt% of catalyst, in only 50 min and with a good reproducibility (±1.1%).

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Dioxiranes. 20. Preparation and properties of some new dioxiranes

Cited by 69 publications

References 0 publications

Reactions of dioxiranes with selected oleochemicals

Reactions of dioxiranes with selected oleochemicals

Continued Progress towards Efficient Functionalization of Natural and Non‐natural Targets under Mild Conditions: Oxygenation by C−H Bond Activation with Dioxirane

Epoxidation of partially norbornylized linseed oil

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