Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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

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: Overview

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...

Base-Catalyzed Ring-Opening of Epoxides

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...

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...

Acid-Catalyzed Ring-Opening of Epoxides

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...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Control over stereogenic centres beyond tetracoordination.

Chemical science·2026

Same author

Enantiospecific Optical Sensing of Terpenes by an Aggregated Atropisomeric Platinum(II) Complex.

Angewandte Chemie (International ed. in English)·2026

Same author

Stereoselective total synthesis of skew-tetramantane.

Nature chemistry·2026

Same author

Determination of the Absolute Configuration by 3D ED to Elucidate the Atroposelectivity in Aromatic Ring-Opening Metathesis.

Chimia·2025

Same author

Atroposelective Arene-Forming Wittig Reaction by Phosphorus P<sup>III</sup>/P<sup>V</sup>=O Redox Catalysis.

Angewandte Chemie (International ed. in English)·2024

Same author

Atroposelective catalysis.

Nature reviews. Chemistry·2024

Same journal

Six ways to put the public at the heart of science and policy.

Nature·2026

Same journal

The complex truth about trust in science.

Nature·2026

Same journal

Have people stopped trusting science? The data tell a surprising story.

Nature·2026

Same journal

How FAIR data are helping to build trust in science.

Nature·2026

Same journal

Scientists should recognize their own political biases to build public trust.

Nature·2026

Same journal

Harmonizing standards and resources for the medical genome.

Nature·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Jun 5, 2025

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

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

Published on: November 29, 2018

Aromatic ring-opening metathesis.

Valeriia Hutskalova¹, Christof Sparr²

¹Department of Chemistry, University of Basel, Basel, Switzerland.

|December 11, 2024

Summary

This summary is machine-generated.

Researchers developed aromatic ring-opening metathesis (ArROM) to cleave stable aromatic carbon-carbon bonds. This novel catalytic method efficiently transforms various aromatic compounds without needing extra reagents or light.

More Related Videos

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Related Experiment Videos

Last Updated: Jun 5, 2025

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

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

Published on: November 29, 2018

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

Organic Chemistry
Catalysis
Materials Science

Background:

Aromatic compounds are vital in chemistry and materials science due to their stability and defined structures.
Cleaving inert aromatic carbon-carbon bonds is challenging due to the energetic cost of disrupting aromaticity.
Alkene metathesis is a powerful tool for non-aromatic systems, but its application to aromatics remained elusive.

Purpose of the Study:

To develop a catalytic method for cleaving aromatic carbon-carbon bonds.
To explore the application of metathesis reactions to aromatic ring systems.
To investigate the potential for stereoselective transformations of aromatics.

Main Methods:

Utilized Schrock-Hoveyda molybdenum catalysts for aromatic ring-opening metathesis (ArROM).
Applied ArROM to various aromatic ring systems, including tetraphene, naphthalene, indole, benzofuran, and phenanthrenes.
Analyzed unique alkylidene intermediates formed during the reactions.

Main Results:

Successfully demonstrated ArROM for the cleavage of diverse aromatic compounds.
Identified unique alkylidene intermediates specific to each aromatic ring system.
Achieved stereoselective ArROM, showcasing catalyst control over atropisomer configuration.

Conclusions:

ArROM provides a viable and efficient catalytic approach to transform aromatic compounds.
This method enables the interconversion of various aromatics without requiring additional reagents or photoexcitation.
The development opens new avenues for manipulating and functionalizing aromatic structures.