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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

1.8K
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...
1.4K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

2.3K
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...
2.3K
Preparation of Epoxides03:00

Preparation of Epoxides

7.6K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
7.6K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
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.
1.4K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.8K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
9.8K

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Related Experiment Video

Updated: Apr 25, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Macrocyclic olefin metathesis at high concentrations by using a phase-separation strategy.

Michaël Raymond1, Michael Holtz-Mulholland, Shawn K Collins

  • 1Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7 (Canada).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 23, 2014
PubMed
Summary

This study introduces a novel phase-separation strategy to overcome dilution effects in macrocyclic olefin metathesis, enabling macrocycle synthesis at higher concentrations. This method efficiently produces diverse macrocyclic structures with various spacers.

Keywords:
homogeneous catalysismacrocyclizationmetathesispoly(ethylene)glycolruthenium

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Macrocyclic olefin metathesis is a key tool for synthesizing macrocycles.
  • Existing methods often require high dilution, limiting efficiency and scalability.
  • Controlling dilution effects in macrocyclization remains a challenge.

Purpose of the Study:

  • To develop a strategy for promoting macrocyclic olefin metathesis at higher concentrations.
  • To overcome the limitations imposed by dilution effects in macrocyclization reactions.

Main Methods:

  • A phase-separation strategy was employed to facilitate macrocyclic olefin metathesis.
  • The protocol was optimized to allow reactions at concentrations up to 60 mM.
  • The method was applied to synthesize various macrocyclic skeletons.

Main Results:

  • Successful macrocyclic olefin metathesis was achieved at significantly higher concentrations than previously reported.
  • The phase-separation strategy effectively mitigated dilution effects.
  • A diverse range of macrocyclic compounds with alkyl, aryl, and amino acid spacers were synthesized.

Conclusions:

  • The described phase-separation protocol is an effective strategy for high-concentration macrocyclic olefin metathesis.
  • This approach enhances the efficiency and practicality of macrocycle synthesis.
  • The method provides access to a variety of macrocyclic structures.