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Related Concept Videos

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

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

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...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...

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Related Experiment Video

Updated: May 16, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

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

Published on: August 23, 2018

Low catalyst loading in ring-closing metathesis reactions.

Renat Kadyrov1

  • 1Evonik Industries AG, Rodenbacher Chaussee 4. renat.kadyrov@evonik.com

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 28, 2012
PubMed
Summary
This summary is machine-generated.

This study presents an efficient ring-closing metathesis procedure using low loadings of ruthenium catalysts with unsaturated N-heterocyclic carbene ligands. It achieves high conversions for diverse heterocyclic compounds, including cyclic amines and lactones.

More Related Videos

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

Related Experiment Videos

Last Updated: May 16, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

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

Published on: August 23, 2018

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Ring-closing metathesis (RCM) is a powerful carbon-carbon bond-forming reaction.
  • Efficient RCM often requires high catalyst loadings or specialized catalysts.
  • Developing more efficient and practical RCM protocols is crucial for organic synthesis.

Purpose of the Study:

  • To describe an efficient procedure for ring-closing metathesis reactions.
  • To utilize commercially available ruthenium catalysts with unsaturated N-heterocyclic carbene (NHC) ligands.
  • To achieve high conversions with very low catalyst loadings.

Main Methods:

  • Employing ruthenium catalysts with unsaturated NHC ligands for RCM.
  • Utilizing diethyl diallylmalonate as a model substrate.
  • Investigating catalyst loading ranging from 50 to 250 ppm.
  • Synthesizing various heterocyclic compounds, including cyclic amines, lactones, and lactams.

Main Results:

  • Achieved 95% conversion of diethyl diallylmalonate in minutes with high turnover frequency (TOF = 4173 min⁻¹).
  • Near-quantitative conversion into 5-16-membered heterocyclic compounds using 50-250 ppm catalyst loading.
  • Successfully synthesized N-Boc- and N-Ts-protected cyclic amines and lactones.
  • Macrocyclic proline-based lactams required slightly higher catalyst loadings.
  • Isolated and characterized oligomeric byproducts, primarily cyclodimers.

Conclusions:

  • The developed RCM procedure is highly efficient, requiring minimal catalyst.
  • This method offers a practical approach for synthesizing a wide range of valuable heterocyclic compounds.
  • The use of readily available Ru catalysts with unsaturated NHC ligands broadens the applicability of RCM.