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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...
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Related Experiment Video

Updated: May 27, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

A highly C70 selective shape-persistent rectangular prism constructed through one-step alkyne metathesis.

Chenxi Zhang1, Qi Wang, Hai Long

  • 1Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309, USA.

Journal of the American Chemical Society
|November 17, 2011
PubMed
Summary

Researchers developed a novel 3-D molecular cage, COP-5, using dynamic covalent chemistry (DCC) and alkyne metathesis. This cage efficiently binds and separates fullerenes, showing high affinity and selectivity for C70 over C60.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

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Last Updated: May 27, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Dynamic covalent chemistry (DCC) offers efficient molecular construction, but methods for complex 3-D architectures are limited.
  • Developing robust methods for creating intricate molecular cages is crucial for advanced applications.

Purpose of the Study:

  • To utilize alkyne metathesis, a DCC approach, for the one-step synthesis of a novel 3-D molecular cage.
  • To investigate the fullerene binding properties of the synthesized cage, focusing on affinity, selectivity, and reversibility.

Main Methods:

  • One-step synthesis of the 3-D rectangular prismatic molecular cage COP-5 using alkyne metathesis.
  • Characterization of COP-5's structure and shape-persistent nature.
  • Spectroscopic analysis to determine binding constants and selectivity for C60 and C70 fullerenes.

Main Results:

  • Successful one-step synthesis of the novel 3-D cage COP-5 from a porphyrin-based precursor.
  • COP-5 exhibits high binding affinity for C60 (1.4 × 10^5 M^-1) and C70 (1.5 × 10^8 M^-1).
  • COP-5 demonstrates exceptional selectivity for C70 over C60 (K(C70)/K(C60) > 1000) and reversible binding under acid-base stimuli.

Conclusions:

  • Alkyne metathesis is a powerful DCC strategy for constructing complex 3-D molecular cages like COP-5.
  • COP-5 represents a highly effective purely organic receptor for fullerenes, with unprecedented C70 selectivity.
  • The reversible binding allows for the separation of C70 from fullerene mixtures, showcasing potential for practical applications.