Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.3K
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...
2.3K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

2.8K
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...
2.8K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.0K
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...
2.0K
Preparation of Epoxides03:00

Preparation of Epoxides

8.4K
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 acids to...
8.4K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.4K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
6.4K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.7K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.7K

You might also read

Related Articles

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

Sort by
Same author

Olefination of Alcohols and Alkyl Halides via Oxidative Alkyl Electrophile-Olefin Metathesis.

Organic letters·2026
Same author

Data-Driven Interrogation of Reactivity in Acid-Catalyzed Carbonyl-Olefin Metathesis with Machine Learning and Large Language Models.

Journal of the American Chemical Society·2026
Same author

Visible-Light-Mediated <i>aza</i> Paternò-Büchi Reactions and Related Cycloadditions for the Formation of Azetidines and Azetines.

Accounts of chemical research·2026
Same author

Interrogating the Carboxylation of Potassium β-Diketonates and β-Diketiminates by Carbon Dioxide.

The Journal of organic chemistry·2026
Same author

Visible-light-mediated synthesis of 2-oxetanes <i>via</i> Giese addition to α-oxy radicals.

Chemical science·2026
Same author

Monocyclic Azetidines via a Visible-Light-Mediated Aza Paternò-Büchi Reaction of Ketone-Derived Sulfonylimines.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Nov 2, 2025

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

9.8K

Carbonyl-Olefin Metathesis.

Haley Albright1, Ashlee J Davis1, Jessica L Gomez-Lopez1

  • 1University of Michigan, Department of Chemistry, Willard Henry Dow Laboratory, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Chemical Reviews
|June 16, 2021
PubMed
Summary

This review details carbonyl-olefin metathesis strategies, evolving from stoichiometric methods to efficient catalytic approaches for complex molecule synthesis. It covers various reactions and their applications, highlighting recent advancements in the field.

More Related Videos

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.5K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.2K

Related Experiment Videos

Last Updated: Nov 2, 2025

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

9.8K
Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.5K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.2K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Carbonyl-olefin metathesis has emerged as a powerful tool in organic synthesis.
  • The field has witnessed significant growth over the past eight years, transitioning from stoichiometric protocols to catalytic strategies.

Purpose of the Study:

  • To provide a comprehensive overview of current carbonyl-olefin metathesis strategies.
  • To capture the status quo of the field and stimulate future advancements.

Main Methods:

  • Paternò-Büchi cycloadditions followed by oxetane fragmentation.
  • Metal alkylidene-mediated strategies.
  • Organocatalytic [3 + 2]-cycloaddition approaches.
  • Lewis acid-mediated and catalyzed strategies via oxetane intermediates.
  • Protocols involving C-C bond formation and Grob-fragmentations.

Main Results:

  • Development of diverse stepwise, stoichiometric, and catalytic methods for carbonyl-olefin metathesis.
  • Expansion of applications in complex molecule synthesis.
  • Significant progress in ring-closing, ring-opening, and cross carbonyl-olefin metathesis.

Conclusions:

  • The field of carbonyl-olefin metathesis has matured significantly, offering efficient catalytic solutions.
  • This review serves as a valuable resource for understanding current methodologies and future directions in carbonyl-olefin metathesis.