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

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.3K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

14.4K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
14.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.3K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
3.3K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

11.7K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
11.7K

You might also read

Related Articles

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

Sort by
Same author

Synthesis of α,β-Unsaturated Diazoketones through the Use of <i>N</i>,<i>N</i>'-Ditosylhydrazine.

The Journal of organic chemistry·2026
Same author

Divergent Total Synthesis of Diterpenoid Natural Products from <i>Salvia miltiorrhiza</i>.

Organic letters·2025
Same author

Strain-Relief-Driven Rearrangement of [2.2]Paracyclophane Derivatives in the Synthesis of Biarylophanes.

Organic letters·2025
Same author

Synthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy.

Organic letters·2024
Same author

UV induced hydrophosphination of dimethyl 2-vinylcyclopropane-1,1-dicarboxylate towards phosphine chalcogenides.

Dalton transactions (Cambridge, England : 2003)·2023
Same author

3,4-Annulated Indoles via Tandem Cyclopropane Ring-Opening/Conia-ene and Michael Addition/Conia-ene Reactions.

Organic letters·2022

Related Experiment Video

Updated: Apr 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.5K

Carbocycles from donor-acceptor cyclopropanes.

Huck K Grover1, Michael R Emmett, Michael A Kerr

  • 1The University of Western Ontario, Department of Chemistry, London, Ontario, Canada N6A 5B7. makerr@uwo.ca.

Organic & Biomolecular Chemistry
|November 27, 2014
PubMed
Summary

This review explores carbocyclic adduct formation using donor-acceptor cyclopropanes. It focuses on acid, base, and thermal reactions, excluding metal-catalyzed processes.

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

8.5K
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

4.1K

Related Experiment Videos

Last Updated: Apr 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.5K
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

8.5K
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

4.1K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Donor-acceptor cyclopropanes are versatile synthetic intermediates.
  • Carbocyclic frameworks are prevalent in natural products and pharmaceuticals.

Purpose of the Study:

  • To review synthetic methodologies for carbocyclic adduct formation from donor-acceptor cyclopropanes.
  • To highlight reactions mediated by Lewis acids, protic acids, bases, and thermal conditions.

Main Methods:

  • Focus on annulation reactions.
  • Focus on cycloaddition reactions (inter- and intramolecular).
  • Exclusion of transition metal-catalyzed reactions and rearrangements.

Main Results:

  • Summarizes key synthetic routes to carbocycles.
  • Details reaction mechanisms under various catalytic conditions.
  • Provides a comprehensive overview of non-metal-mediated transformations.

Conclusions:

  • Donor-acceptor cyclopropanes offer efficient pathways to carbocyclic structures.
  • Acid, base, and thermal conditions are effective for cyclopropane-mediated annulations and cycloadditions.
  • This review consolidates essential non-metal-catalyzed methods for carbocycle synthesis.