Metal-catalysed Oxidation of Organic Compounds by Hydroperoxides

Толстиков, Г. А.; Yur'ev, V. P.; Джемилев, У. М.

doi:10.1070/rc1975v044n04abeh002270

Cited by 28 publications

(12 citation statements)

References 26 publications

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“…Epoxidations with hydrogen peroxide 9 (15) M=Mo, W An intramolecular, concerted rearrangement of an allylic pertungstate ester has been proposed [34] to account for the exceptional reactivity of allylic alcohols to W(VI)/H 2 0 2 . We note that the transition state for the second mechanism would appear to have a more favourable geometry for such an intramolecular oxygen transfer, as is illustrated below*.…”

Section: M=mo Wmentioning

confidence: 99%

“…Soluble complexes of molybdenum, tungsten and, to a lesser extent, vanadium and titanium have been shown to be particularly active catalysts for the selective epoxidation of olefins with alkyl hydroperoxides [14,15]. The high yields of epoxides obtained with a wide variety of olefins and the sterospecificity of these reactions are consistent only with a heterolytic mechanism.…”

Section: Factors Governing Catalyst Activity and Selectivitymentioning

confidence: 99%

“…79) [15]. For example, 4-cyanocyclohexene is smoothly epoxidized to give an 89% yield of the epoxide (Eq.…”

Section: Effect Of Olefin Structure On Reactivitymentioning

confidence: 99%

“…The subject of metal-catalysed epoxidations with alkyl hydroperoxides was reviewed by Hiatt [14] in 1971 and, more recently, by Tolstikov et al [15], Rouchaud [16] and Metelitza [17]. However, since these publications appeared, much more information has become available, particularly on the mechanistic aspects and on the scope of this versatile reaction in organic synthesis.…”

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confidence: 99%

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Metal-Catalysed Epoxidations of Olefins with Hydroperoxides

Sheldon

1981

Aspects of Homogeneous Catalysis

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Section: M=mo Wmentioning

confidence: 99%

Section: Factors Governing Catalyst Activity and Selectivitymentioning

confidence: 99%

“…79) [15]. For example, 4-cyanocyclohexene is smoothly epoxidized to give an 89% yield of the epoxide (Eq.…”

Section: Effect Of Olefin Structure On Reactivitymentioning

confidence: 99%

mentioning

confidence: 99%

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Metal-Catalysed Epoxidations of Olefins with Hydroperoxides

Sheldon

1981

Aspects of Homogeneous Catalysis

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“…One of the most important applications of hydroperoxides is in the catalytic epoxidation of olefins [3][4][5][6]. The epoxides obtained from such reactions are used for the synthesis of many useful oxygen-containing products [7,8].…”

Section: Introductionmentioning

confidence: 99%

FTIR investigation into transition metal disilicides as catalysts for tert-butyl hydroperoxide decomposition

Trach

Makota

Skubiszewska–Zięba

et al. 2010

Transition Met Chem

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Disilicides of molybdenum, tungsten, tantalum, and titanium were studied using FTIR spectroscopy to establish the origin of their different catalytic activities in the decomposition of tert-butyl hydroperoxide. The FTIR spectra of the metal disilicides before and after the decomposition reaction show that their different catalytic activities are caused not only by the nature of the transition metal, but also by different abilities of their surfaces to adsorb water. The increase in the catalyst's ability to adsorb water leads to a decrease in catalyst activity.

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Epoxidation – Homogeneous

Merlau

Borg‐Breen

Nguyen

2002

Encyclopedia of Catalysis

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In this article, catalyst systems for homogeneous epoxidation are reviewed with an emphasis on reaction elements that are of foremost interest to synthetic chemists: catalyst systems, substrate scope, and selectivity. General mechanisms and reaction conditions for each catalyst system are discussed followed by more detailed summaries of the epoxidation of specific classes of olefins: unfunctionalized terminal olefins, cis‐disubstituted, trans‐disubstituted, tri‐ and tetrasubstituted olefins, functionalized olefins including allylic alcohols, and electron‐deficient olefins. Major classes of catalysts addressed are early transition metal‐peroxo forming catalysts (inclusive of the Sharpless titanium tartrate catalyst for the asymmetric epoxidation of allylic alcohols and MTO), metal‐oxo forming catalysts (such as metalloporphyrin and Jacobsen/Katsuki salen catalysts), dioxirane and oxaziridine catalysts, Lewis acid and lanthanide catalysts, phase‐transfer and polyamino acid catalysts, and finally sulfur ylide catalysts for the formation of epoxides from aldehydes. Dedicated to Professor K. Barry Sharpless on the occasion of his 60th birthday.

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Metal-catalysed Oxidation of Organic Compounds by Hydroperoxides

Cited by 28 publications

References 26 publications

Metal-Catalysed Epoxidations of Olefins with Hydroperoxides

Metal-Catalysed Epoxidations of Olefins with Hydroperoxides

FTIR investigation into transition metal disilicides as catalysts for tert-butyl hydroperoxide decomposition

Epoxidation – Homogeneous

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