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Related Concept Videos

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...
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...
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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Related Experiment Video

Updated: May 19, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Fast olefin metathesis at low catalyst loading.

Lars H Peeck1, Roman D Savka, Herbert Plenio

  • 1Organometallic Chemistry, Technische Universität Darmstadt, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 30, 2012
PubMed
Summary
This summary is machine-generated.

New N-Grubbs-Hoveyda-type complexes exhibit rapid catalyst activation for efficient ring-closing metathesis (RCM). These novel catalysts, particularly complexes 8 and 9, demonstrate high activity and yields in synthesizing various cyclic compounds.

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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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Last Updated: May 19, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Grubbs catalysts are crucial for olefin metathesis reactions.
  • Development of N-Grubbs-Hoveyda-type complexes offers potential improvements over traditional O-Grubbs-Hoveyda complexes.
  • N-heterocyclic carbene (NHC) ligands significantly influence catalyst performance.

Purpose of the Study:

  • To synthesize and characterize novel N-Grubbs-Hoveyda-type ruthenium complexes.
  • To evaluate the catalytic activity of these new complexes in ring-closing metathesis (RCM).
  • To compare the performance of N-Grubbs-Hoveyda complexes with their O-Grubbs-Hoveyda counterparts.

Main Methods:

  • Synthesis of Grubbs 3rd generation complexes with varying NHC ligands (SIMes, SIPr, IPr).
  • Reaction of these complexes with 2-ethenyl-N-alkylaniline to form N-chelating benzylidene ligands.
  • Evaluation of catalytic activity in RCM reactions using low catalyst loadings and short reaction times.

Main Results:

  • Formation of five new N-Grubbs-Hoveyda-type complexes (5-9) in 50-75% yields.
  • Exhibited fast catalyst activation leading to efficient RCM.
  • Complexes 8 and 9 showed the highest catalytic activity, enabling RCM with low catalyst loadings (15-150 ppm) and short reaction times (15 min).
  • High yields (83-92%) and excellent turnover numbers (TONs) and turnover frequencies (TOFs) were achieved for various cyclic compounds.

Conclusions:

  • The new N-Grubbs-Hoveyda-type complexes are highly active and efficient catalysts for RCM.
  • Complexes 8 and 9 represent a significant advancement in ruthenium-catalyzed RCM.
  • These findings open avenues for more sustainable and efficient synthesis of nitrogen-containing heterocycles.