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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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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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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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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Related Experiment Video

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Tandem Catalysis Utilizing Olefin Metathesis Reactions.

Grzegorz K Zieliński1, Karol Grela2,3

  • 1Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland. grzesiek.zielinski88@gmail.com.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 21, 2016
PubMed
Summary

Ruthenium catalysts efficiently perform olefin metathesis and other reactions, like isomerization and hydrogenation. These reactions can be combined in tandem catalysis for complex synthesis from simple starting materials.

Keywords:
homogeneous catalysisnatural productsolefin metathesisrutheniumtandem processes

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Olefin metathesis is a key synthetic tool in organic synthesis.
  • Ruthenium catalysts are versatile, promoting various non-metathetical reactions beyond olefin metathesis.
  • These reactions include isomerization, hydrogenation, and oxidation.

Purpose of the Study:

  • To discuss tandem catalysis involving olefin metathesis.
  • To highlight the synthetic value of these tandem processes.
  • To clarify the definition of tandem processes in the literature.

Main Methods:

  • Review of literature examples of tandem catalysis with olefin metathesis.
  • Emphasis on the synthetic utility and practical aspects of these reactions.
  • Discussion of catalyst versatility under different reaction conditions.

Main Results:

  • Ruthenium catalysts can promote multiple reaction types, including olefin metathesis, isomerization, and hydrogenation.
  • Tandem catalysis allows for the synthesis of complex products from simple substrates in one pot.
  • The term "tandem process" is sometimes misapplied in the literature.

Conclusions:

  • Tandem catalysis involving olefin metathesis offers significant synthetic advantages.
  • These processes streamline synthesis, reducing intermediate isolation steps.
  • Proper application of tandem catalysis opens new retrosynthetic planning strategies.