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

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Acid Halides to Esters: Alcoholysis

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium,...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

You might also read

Related Articles

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

Sort by

Same author

Intubation Prior to Tetralogy of Fallot with Absent Pulmonary Valve Surgery: A Tale of Two Ventilation Pathways.

Pediatric cardiology·2026

Same author

A low-dose self-amplifying mRNA vaccine encoding HPV16 E6/E7 induces potent T-cell immunity and antitumor protection in mice.

Cancer immunology, immunotherapy : CII·2026

Same author

The Role of 5-HT and DA Receptor Genes in Starvation-Induced Anxiety Behavior of <i>Portunus trituberculatus</i>.

Genes·2026

Same author

Impact of exposure to metallic elements on gestational diabetes mellitus: Insights from human investigations.

Ecotoxicology and environmental safety·2026

Same author

miR-150 controls developmental angiogenesis via ribosome biogenesis-dependent regulation of Notch signaling.

Angiogenesis·2026

Same author

Nitrate boosts arsenic accumulation in hyperaccumulator Pteris vittata by coupling nitrogen assimilation with arsenic detoxification.

Journal of hazardous materials·2026

Search research articles

Related Experiment Video

Updated: Dec 16, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Sulfoxide Reduction/C(sp³)-S Metathesis Cascade in Ionic Liquid.

Chenjing Liu¹, Dengfeng Chen¹, Yuanyuan Fu¹

¹Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, People's Republic of China.

Organic Letters

|July 3, 2020

Summary

A novel sulfoxide reduction and C-S bond metathesis cascade efficiently synthesizes valuable sulfides from sulfoxides and alkyl bromides. This catalyst- and base-free method utilizes ionic liquids for sustainable synthesis.

More Related Videos

Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Published on: December 20, 2016

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Related Experiment Videos

Last Updated: Dec 16, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Published on: December 20, 2016

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

Organic Chemistry
Sustainable Chemistry

Background:

Sulfides are crucial in pharmaceuticals and materials science.
Existing synthesis methods often require harsh conditions, catalysts, or bases.

Purpose of the Study:

To develop a novel, efficient, and sustainable method for synthesizing high-value sulfides.
To explore a catalyst- and base-free cascade reaction for sulfide synthesis.

Main Methods:

A sulfoxide reduction/C-S bond metathesis cascade reaction was developed.
The reaction employs classical Kornblum oxidation within an ionic liquid medium.
Sulfoxides were reacted with alkyl bromides under mild conditions.

Main Results:

High-value sulfides were successfully synthesized without catalysts or bases.
The protocol demonstrated high functional group tolerance.
The reaction showed promising scalability and utilized sustainable solvents.

Conclusions:

The developed cascade reaction offers an efficient and green alternative for sulfide synthesis.
This method avoids the need for potentially toxic or expensive catalysts and bases.
The use of ionic liquids contributes to the sustainability of the process.