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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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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

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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Tandem Ring-Opening-Ring-Closing Metathesis for Functional Metathesis Catalysts.

Amit A Nagarkar1, Mohammad Yasir1, Aurelien Crochet1

  • 1Department of Chemistry, University of Fribourg, Chemin du Musee 9, 1700, Fribourg, Switzerland.

Angewandte Chemie (International Ed. in English)
|September 6, 2016
PubMed
Summary

A novel tandem ring-opening-ring-closing metathesis strategy efficiently synthesizes functional metathesis catalysts. This method yields hydroxy-functionalized Grubbs

Keywords:
Grubbs catalystsheterotelechelic polymersolefin metathesispolymerizationruthenium

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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Materials Science

Background:

  • Metathesis catalysts are crucial for synthesizing functional materials.
  • Existing methods for catalyst synthesis can be inefficient or limited in scope.

Purpose of the Study:

  • To develop an efficient and versatile strategy for synthesizing functional metathesis catalysts.
  • To create new generations of Grubbs' catalysts with enhanced properties.

Main Methods:

  • Utilized a tandem ring-opening-ring-closing metathesis (RORCM) strategy.
  • Employed commercially available Grubbs' catalysts as starting materials.
  • Performed mechanistic studies to understand reaction pathways.

Main Results:

  • Successfully synthesized hydroxy-functionalized Grubbs' first- and third-generation catalysts.
  • Demonstrated the efficiency of the RORCM strategy for catalyst preparation.
  • Synthesized the ruthenium methylidene complex using this approach.

Conclusions:

  • The reported RORCM strategy provides an efficient route to novel functional metathesis catalysts.
  • This method expands the toolkit for catalyst design and synthesis.
  • The synthesized catalysts hold potential for various applications in organic synthesis and materials science.