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

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.

Electrophilic Aromatic Substitution: Overview

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.

Radical Autoxidation

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...

Electrolysis

Electrolysis

In a galvanic cell, the electrical work is done by a redox system on its surroundings as electrons produced by the spontaneous redox reactions are transferred through an external circuit. Alternatively, an external circuit does work on a redox system by imposing a voltage sufficient to drive an otherwise nonspontaneous reaction in a process known as electrolysis. For instance, recharging a battery involves the use of an external power source to drive the spontaneous (discharge) cell reaction in...

Introduction to Chemical Reactions

Introduction to Chemical Reactions

All chemical reactions begin with a reactant, the general term for one or more substances entering the reaction. Sodium and chloride ions, for example, are the reactants in the production of table salt. One or more substances produced by a chemical reaction are called the product. Chemical reactions follow the law of conservation of mass, which means that matter cannot be created nor destroyed in a chemical reaction. The components of the reactants—the number of atoms and the elements—are all...

Radical Reactivity: Overview

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...

You might also read

Related Articles

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

Sort by

Same author

Synthetic study of <i>vic</i>-bromination of diarylacetylenes, easy purification and separation.

Beilstein journal of organic chemistry·2026

Same author

Synthesis of thienoacenes by electrochemical double C-S cyclization using a halogen mediator.

Communications chemistry·2025

Same author

Bioinspired Electrochemical Cyclization toward the Divergent Synthesis of Mavacurane- and Akuammiline-Type Alkaloids.

Organic letters·2025

Same author

Synthesis of <i>N</i>,<i>O</i>-Bidentate Difluoroboron Complexes via Iodide-Promoted Demethylative Borylation.

Organic letters·2025

Same author

Electrochemical Generation of Sulfonamidyl Radicals via Anodic Oxidation of Hydrogen Bonding Complexes: Applications to Electrosynthesis of Benzosultams.

JACS Au·2025

Same author

Transformation of α,β-Unsaturated Aldehydes with a Small Amount of Electricity: Cyanosilylation, Isomerization, and Nucleophilic Addition.

Organic letters·2025

Search research articles

Related Experiment Video

Updated: Jun 4, 2026

Self-standing Electrochemical Set-up to Enrich Anode-respiring Bacteria On-site

Self-standing Electrochemical Set-up to Enrich Anode-respiring Bacteria On-site

Published on: July 24, 2018

Organic reactions mediated by electrochemically generated ArS+.

Kouichi Matsumoto¹, Seiji Suga, Jun-ichi Yoshida

¹Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. kmatsumo@chem.kindai.ac.jp

Organic & Biomolecular Chemistry

|February 26, 2011

Summary

Electrochemical oxidation of diaryl disulfides generates a reactive "ArS(+)" species. This species enables efficient synthesis of diarylthio-substituted compounds and thiochromans via novel cationic pathways.

More Related Videos

Electrochemically and Bioelectrochemically Induced Ammonium Recovery

Electrochemically and Bioelectrochemically Induced Ammonium Recovery

Published on: January 22, 2015

Tracking Electrochemistry on Single Nanoparticles with Surface-Enhanced Raman Scattering Spectroscopy and Microscopy

Tracking Electrochemistry on Single Nanoparticles with Surface-Enhanced Raman Scattering Spectroscopy and Microscopy

Published on: May 12, 2023

Related Experiment Videos

Last Updated: Jun 4, 2026

Self-standing Electrochemical Set-up to Enrich Anode-respiring Bacteria On-site

Self-standing Electrochemical Set-up to Enrich Anode-respiring Bacteria On-site

Published on: July 24, 2018

Electrochemically and Bioelectrochemically Induced Ammonium Recovery

Electrochemically and Bioelectrochemically Induced Ammonium Recovery

Published on: January 22, 2015

Tracking Electrochemistry on Single Nanoparticles with Surface-Enhanced Raman Scattering Spectroscopy and Microscopy

Tracking Electrochemistry on Single Nanoparticles with Surface-Enhanced Raman Scattering Spectroscopy and Microscopy

Published on: May 12, 2023

Area of Science:

Organic Chemistry
Electrochemistry
Synthetic Methodology

Background:

Electrophilic sulfur reagents are crucial in organic synthesis.
Developing new methods for generating and utilizing reactive sulfur species is an active research area.
Electrochemical methods offer sustainable and controlled approaches to generate reactive intermediates.

Purpose of the Study:

To explore the low-temperature electrochemical oxidation of diaryl disulfides (ArSSAr) to generate electrophilic "ArS(+)" species.
To investigate the reactivity of the generated "ArS(+)" pool with various unsaturated substrates and nucleophiles.
To develop new synthetic routes for diarylthio-substituted compounds and heterocyclic structures.

Main Methods:

Low-temperature electrochemical oxidation of ArSSAr.
Spectroscopic characterization (¹H NMR, CSI-MS) of reaction intermediates.
Reactions with alkenes, alkynes, thioacetals, and stilbene derivatives.
Exploration of catalytic cationic chain reactions initiated by "ArS(+)".

Main Results:

Successful generation and characterization of the "ArS(+)" pool and its adducts.
Efficient synthesis of diarylthio-substituted alkenes and alkynes.
Development of an indirect cation pool method using thioacetals for nucleophilic additions.
Synthesis of thiochroman derivatives via reaction with stilbenes.
Demonstration of "ArS(+)" as an initiator for catalytic cationic chain reactions.

Conclusions:

Low-temperature electrochemical oxidation provides a facile route to reactive "ArS(+)" species.
The "ArS(+)" pool is a versatile intermediate for synthesizing diverse sulfur-containing organic molecules.
"ArS(+)" can initiate and propagate cationic chain reactions, enabling efficient C-C bond formation.