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

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.1K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.1K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.5K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.5K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.3K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
2.3K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.2K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.3K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.3K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

12.5K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
12.5K

You might also read

Related Articles

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

Sort by
Same author

3-Azetidinylpiperidine-4-alkylidenemalononitrile and Related Building Blocks.

Organic letters·2026
Same author

Synthesis of 1,3-Bis-trifluoromethylated (Hetero)cyclohexane-2-carboxylates from Alkylidenemalononitriles.

Organic letters·2026
Same author

Teaching an Old Dog New Tricks for Achieving CB<sub>2</sub>-Selective Inverse Agonism.

ACS central science·2024
Same author

Three-Component <i>cine</i>,<i>ipso</i>-Disubstitution of Nitrocoumarins.

Organic letters·2024
Same author

Axially Chiral Cannabinoids: Design, Synthesis, and Cannabinoid Receptor Affinity.

Journal of the American Chemical Society·2023
Same author

Vicinal stereocenters <i>via</i> asymmetric allylic alkylation and Cope rearrangement: a straightforward route to functionally and stereochemically rich heterocycles.

Chemical science·2023
Same journal

Catalytic synthesis of saturated azacycles using transborylation.

Organic & biomolecular chemistry·2026
Same journal

Pyridines with adamantane fragments and their 1,2,4-triazine analogues as anti-quorum-sensing agents, synthesis and molecular docking.

Organic & biomolecular chemistry·2026
Same journal

Synthesis of polymethylene-linked bis(cyclobutane-fused chromanones) mediated by gold photocatalysis.

Organic & biomolecular chemistry·2026
Same journal

Palladium-catalyzed chelation-assisted C-H functionalization of quinoline aldehydes to esters with mechanistic insights.

Organic & biomolecular chemistry·2026
Same journal

One-pot metal-free access to uracil-benzofuran bis-heterocycles: synthesis and DFT insights.

Organic & biomolecular chemistry·2026
Same journal

Transition-metal-free three-component synthesis of α-tertiary trifluoromethyl phosphonates from CF<sub>3</sub> diazo compounds.

Organic & biomolecular chemistry·2026
See all related articles

Related Experiment Video

Updated: Nov 15, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.8K

Aromatic Cope rearrangements.

Breanna M Tomiczek1, Alexander J Grenning

  • 1Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, USA. grenning@ufl.edu.

Organic & Biomolecular Chemistry
|March 2, 2021
PubMed
Summary
This summary is machine-generated.

The aromatic Cope rearrangement, a specialized reaction involving aromatic systems, remains underdeveloped compared to standard Cope rearrangements. This review highlights key substrates and challenges, advocating for its further study in arene functionalization.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.2K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.5K

Related Experiment Videos

Last Updated: Nov 15, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.8K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.2K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.5K

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Synthetic Methodology

Background:

  • The Cope rearrangement of 1,5-dienes is a versatile synthetic tool.
  • Aromatic Cope rearrangements, involving aromatic systems, are less explored.
  • Understanding these reactions is crucial for advancing organic synthesis.

Purpose of the Study:

  • To review the literature on aromatic Cope rearrangements since 1956.
  • To identify kinetic and thermodynamic challenges.
  • To categorize key substrate features for this transformation.

Main Methods:

  • Literature review of approximately 40 papers.
  • Categorization of aromatic Cope rearrangement substrates.
  • Analysis of kinetic and thermodynamic factors.

Main Results:

  • Identified four main types of substrates: α-allyl-α-aryl malonates, 1-aryl-2-vinylcyclopropanes, anion-accelerated aromatic oxy-Cope substrates, and synchronized aromaticity.
  • Highlighted kinetic and thermodynamic hurdles.
  • Summarized historical development and applications.

Conclusions:

  • Aromatic Cope rearrangements offer potential for arene functionalization.
  • Further research and development are needed to unlock its synthetic utility.
  • This review aims to stimulate interest in this underutilized reaction.