Metal Acetylacetonate Catalyzed Epoxidation of Olefins with t-Butyl Hydroperoxide

Indictor, N.

doi:10.1021/jo01017a520

Cited by 98 publications

(16 citation statements)

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“…It can be also seen from Table 2 that EPDM has the highest epoxidation level and the highest efficiency of TBHP. The earlier experimental results provided by others [20] have shown that the epoxidation rate of catalytic epoxidation of olefins is influenced by the structure of double bonds. Increasing alkyl substitution enhances the relative reactivities of double bonds.…”

Section: Effect Of the Structure Of Unsaturated Rubbersmentioning

confidence: 86%

Epoxidation of Unsaturated Rubbers with Alkyl Hydroperoxide using Molybdenum Compounds as Catalyst in the Reactive Processing Equipment

Zhang¹,

Chen

Zhang

et al. 2001

Macromol. Mater. Eng.

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Section: Effect Of the Structure Of Unsaturated Rubbersmentioning

confidence: 86%

Epoxidation of Unsaturated Rubbers with Alkyl Hydroperoxide using Molybdenum Compounds as Catalyst in the Reactive Processing Equipment

Zhang¹,

Chen

Zhang

et al. 2001

Macromol. Mater. Eng.

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“…Acetylacetonate complexes of molybdenum and vanadium, known catalysts for olefin epoxidation ( 16,17), were unsuitable for TME oxida tion at 50 °C. No observable reaction occurred after 4-hour periods with these complexes.…”

Section: Resultsmentioning

confidence: 99%

Oxidation of Olefins in the Presence of Transition Metal Complexes

Lyons

1974

Advances in Chemistry

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With certain metal complexes the product profile resulting from olefin oxidation differs greatly from that of classical autoxidation. Reactions carried out in the presence of cer tain metal complexes are highly selective in forming one product or a single set of products. When group VIII metal complexes are used, α,β unsaturated alcohols and ketones predominate. With molybdenum, epoxides are formed in high yield; with vanadium complexes, epoxy alcohols are formed. The oxidation of substituted olefins by the com plexes which we studied proceeds via an allylic hydroper oxide intermediate. The observed products are a function of the selective decomposition of the allylic hydroperoxide by the metal complex. In the decomposition of allylic hydroperoxides the products obtained with a given complex parallel the results of oxidation. Manytransition metal complexes react reversibly with molecular oxygen (1, 2) and with olefins (3, 4, 5). van Gaal et al. (6) recently prepared a group VIII metal complex which contains both oxygen and an olefin in the coordination sphere (Reaction 1).(1) L = PPh; PPh3 64

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“…Therefore an effort has been made in the past years to deduce the structure of the species in solution from indirect evidence, mainly kinetic and spectroscopic [37][38][39][40][41][42][43][44][45][46][47]. The resulting picture may not be very accurate but it certainly offers a rationale to the different behavior observed.…”

Section: B Peroxo Complexes In Solutionmentioning

confidence: 99%

“…(37) involves an unproductive association of the substrate to the metalperoxo (seeScheme 19) generating several species of decreasing reactivity, e.~. k~ << k 2[73].Also, studies on the presence of variable amounts of a strong ligand, which depress reaction rates considerably, may be fitted to equations derived from the above cited hypothesis although in this case a better fit is obtained on the basis of Eq (37)[94].…”

mentioning

confidence: 99%