Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-reactant

Payne, George B.; Deming, P.; Williams, Paul H.

doi:10.1021/jo01062a004

Cited by 316 publications

(118 citation statements)

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“…The more traditional synthetic pathway is the alkali-catalyzed epoxidation and oxidation using a nitrile as coreactant (Payne, Deming, & Williams 1961). This preparation turns out to be time consuming with a yield of less than 60%.…”

Section: Experimental Considerationsmentioning

confidence: 99%

The Millimeter‐ and Submillimeter‐Wave Spectrum of Oxiranecarbonitrile

Behnke¹,

Medvedev²,

Winnewisser³

et al. 2004

ASTROPHYS J SUPPL S

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A number of nitrogen-containing organic molecules, such as the cyanopolyynes, have been detected in dense interstellar clouds, and saturated species such as ethyl cyanide (CH 3 CH 2 CN) have been found in ''hot-core'' type sources. One nitrogen-containing molecule of special interest is the pre-biotic three-membered ring species oxiranecarbonitrile (c-C 3 H 3 NO). A prior attempt to detect this species toward a variety of sources failed, but this attempt was based on low-frequency laboratory data. To facilitate a more effective interstellar search, we have studied the millimeter-and submillimeter-wave spectrum of the vibrational ground state of oxiranecarbonitrile. With the fast-scan submillimeter spectroscopic technique (FASSST), we have measured and analyzed over 1300 new spectral lines at frequencies up to 360 GHz. Fitting the data to a set of spectroscopic parameters from the Watson A-reduced form of the asymmetric-top Hamiltonian has allowed us to predict the frequencies and intensities of many more transitions through 400 GHz.

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Section: Experimental Considerationsmentioning

confidence: 99%

The Millimeter‐ and Submillimeter‐Wave Spectrum of Oxiranecarbonitrile

Behnke¹,

Medvedev²,

Winnewisser³

et al. 2004

ASTROPHYS J SUPPL S

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“…[1][2][3][4] It is known that the conventional preparation of pyridine N-oxides employs a non-catalytic oxidation process using dioxiranes, [5] activated H2O2, [6] H2SO5 (Caro's acid) [7] and magnesium monophthalate [8] or peracids [9,10] as oxidants. However, these reagents not only are highly corrosive, but also generate large amounts of wastes during the reaction process which require frequent and laborious work-up treatments.…”

Section: Introductionmentioning

confidence: 99%

Facile Immobilization of a Lewis Acid Polyoxometalate onto Layered Double Hydroxides for Highly Efficient N‐Oxidation of Pyridine‐Based Derivatives and Denitrogenation

Yao

Miras

et al. 2015

ChemCatChem

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N-Oxides are a class of highly important compounds which are widely used as synthetic intermediates. In this paper, we demonstrate for the first time the use of a polyoxometalate (POM) based composite material, as highly efficient heterogeneous catalyst for the N-oxidation of pyridines and its derivatives in the presence of H2O2 at room temperature. The composite was prepared by intercalation of the [La(PW11O39)2] 11-anion into a tris(hydroxymethyl)aminomethane (Tris) modified layered double hydroxides (LDHs). Additionally, the Tris-LDH-La(PW11)2-based catalyst has been employed for the denitrogenation of a model oil mixture in the presence of [bmim]BF4 and H2O2. Deep denitrogenation can be achieved in 40 minutes at 75 °C. Finally, the heterogeneous catalyst can be easily recovered and reused at least ten times without measurable decrease of the catalytic activity and disintegration of the Tris-LDH-La(PW11)2 structure.

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“…However, the GNPs-RuO 2 NRs showed less catalytic activity in the N-oxidation reactions. Hence, herein, 10 we report the simple preparation of graphene nanoplatelets (GNPs) supported ultrafine RuO 2 NPs catalyst and its activity towards N-oxidation of tertiary amines.…”

Section: Introductionmentioning

confidence: 99%

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

Gopiraman¹,

Bang²,

Babu³

et al. 2014

Catal. Sci. Technol.

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Ultrafine ruthenium oxide nanoparticles (RuO 2 NPs) of an average diameter of 1.3 nm were anchored on graphene nanoplatelets (GNPs) using Ru(acac) 3 precursor by a very simple dry synthesis method. The resultant material (GNPs-RuO 2 NPs) was used as a heterogeneous catalyst for the N-oxidation of tertiary amines for the first time. The transmission electron microscopic (TEM) images of the GNPs-RuO 2 NPs 10 showed an excellent attachment of RuO 2 NPs on GNPs. The loading of Ru in GNPs-RuO 2 NPs was 2.68 wt%, as confirmed by scanning electron microscope-energy dispersive spectroscopy (SEM-EDS). X-ray photoelectron spectrum (XPS) and X-ray diffraction pattern (XRD) of GNPs-RuO 2 NPs revealed that the chemical state of Ru on GNPs was +4. After the optimization of reaction conditions for N-oxidation of triethylamine, the scope of the reaction was extended with a various aliphatic, alicyclic and aromatic 15 tertiary amines. The GNPs-RuO 2 NPs showed an excellent catalytic activity in terms of yields even at a very low amount of Ru catalyst (0.13 mol%). The GNPs-RuO 2 NPs was heterogeneous in nature, chemically as well as physically very stable and reused for up to 5 times.

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Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-reactant

Cited by 316 publications

References 1 publication

The Millimeter‐ and Submillimeter‐Wave Spectrum of Oxiranecarbonitrile

The Millimeter‐ and Submillimeter‐Wave Spectrum of Oxiranecarbonitrile

Facile Immobilization of a Lewis Acid Polyoxometalate onto Layered Double Hydroxides for Highly Efficient N‐Oxidation of Pyridine‐Based Derivatives and Denitrogenation

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

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