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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Vanadyl cationic complexes as catalysts in olefin oxidation.

Carla D Nunes1, Pedro D Vaz, Vítor Félix

  • 1Centro de Química e Bioquímica, DQB, Faculdade de Ciências, Universidade de Lisboa, 1749-016 Lisboa, Portugal. mjc@ciencias.ulisboa.pt.

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|February 13, 2015
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Summary

New oxovanadium(IV) complexes catalyze olefin epoxidation using tert-butylhydroperoxide and hydrogen peroxide. These catalysts show high turnover frequencies and selectivity, particularly for enantiopure olefins, with mechanistic insights revealing associative pathways.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Oxidation Reactions

Background:

  • Oxovanadium(IV) complexes are known catalysts for oxidation reactions.
  • Epoxidation of olefins is a crucial transformation in organic synthesis.
  • Developing efficient and selective epoxidation catalysts remains an active area of research.

Purpose of the Study:

  • To synthesize and characterize novel mononuclear oxovanadium(IV) complexes.
  • To evaluate the catalytic activity of these complexes in olefin epoxidation.
  • To investigate the selectivity and mechanistic aspects of the epoxidation reactions.

Main Methods:

  • Synthesis and characterization of three new mononuclear oxovanadium(IV) complexes.
  • Catalytic testing for the oxidation of various olefins using tert-butylhydroperoxide (tbhp) and hydrogen peroxide (H2O2).
  • Kinetic studies, Electron Paramagnetic Resonance (EPR) spectroscopy, cyclic voltammetry, and Density Functional Theory (DFT) calculations for mechanistic investigations.

Main Results:

  • The synthesized oxovanadium(IV) complexes effectively catalyzed the epoxidation of cyclohexene, cis-cyclooctene, and styrene.
  • Selective epoxidation of enantiopure olefins (pinene and limonene) was achieved using tbhp as the oxidant.
  • High turnover frequencies were observed for specific substrate-catalyst combinations, with up to 90% conversion in some systems.
  • Kinetic data and DFT calculations suggest an associative mechanism involving a [VO(H-BIAN)(MeOO)](+) species as the active intermediate.

Conclusions:

  • The new mononuclear oxovanadium(IV) complexes are efficient catalysts for olefin epoxidation.
  • The catalysts exhibit good selectivity, especially for enantiopure olefins.
  • Mechanistic studies provide insights into the catalytic cycle, highlighting associative pathways and the active V(IV) species.