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

Cationic Chain-Growth Polymerization: Mechanism

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

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 rearrangements are...

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.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

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.

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

You might also read

Related Articles

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

Sort by

Same author

Correction to "Strain Release Cycloadditions of 2H-Azirines: Access to Polycyclic Heterocycles".

Organic letters·2026

Same author

Strain Release Cycloadditions of 2H-Azirines: Access to Polycyclic Heterocycles.

Organic letters·2025

Same author

TPDYs: strained macrocyclic diynes for bioconjugation processes.

Chemical communications (Cambridge, England)·2024

Same author

Tuning Co-Operative Energy Transfer in Copper(I) Complexes Using Two-Photon Absorbing Diimine-Based Ligand Sensitizers.

Angewandte Chemie (International ed. in English)·2024

Same author

Photocatalytic Thiol-Yne Reactions of Alkynyl Sulfides.

The Journal of organic chemistry·2023

Same author

Heteroleptic Copper(I)-Based Complexes Incorporating BINAP and π-Extended Diimines: Synthesis, Catalysis and Biological Applications.

Molecules (Basel, Switzerland)·2022

Search research articles

Related Experiment Video

Updated: Jun 9, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene

Philippe Bolduc¹, Alexandre Jacques, Shawn K Collins

¹Université de Montréal, Département de Chimie, C.P. 6128 Station Downtown, Montréal, Québec, H3C 3J7, Canada.

Journal of the American Chemical Society

|August 27, 2010

Summary

This summary is machine-generated.

Quinolinium salt 3 effectively promotes macrocyclization for rigid cyclophane synthesis using olefin metathesis or Glaser-Hay coupling. This conformation control element (CCE) is easily synthesized, modifiable, and recoverable.

More Related Videos

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Related Experiment Videos

Last Updated: Jun 9, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Macrocyclization is crucial for synthesizing complex molecular architectures.
Traditional methods often struggle with forming rigid cyclophanes efficiently.

Purpose of the Study:

To introduce a novel additive, Quinolinium salt 3, as a conformation control element (CCE).
To demonstrate the utility of CCEs in promoting macrocyclization reactions.

Main Methods:

Utilizing Quinolinium salt 3 in olefin metathesis reactions.
Employing Quinolinium salt 3 in Glaser-Hay coupling reactions.
Characterizing the resulting rigid cyclophanes.

Main Results:

Quinolinium salt 3 significantly enhances macrocyclization yields for rigid cyclophanes.
The additive facilitates cyclization in reactions that otherwise fail.
The CCE is easily synthesized, modifiable, and recoverable via filtration.

Conclusions:

Quinolinium salt 3 is a versatile and effective additive for macrocyclization.
This approach provides a new strategy for constructing rigid cyclophanes.
The developed additives offer practical advantages in synthesis and purification.