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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.

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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.

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Structure and Nomenclature of Thiols and Sulfides

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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...

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Updated: Jun 27, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Published on: November 22, 2016

Phosphine-catalyzed disulfide metathesis.

Rémi Caraballo¹, Martin Rahm, Pornrapee Vongvilai

¹Royal Institute of Technology, Department of Chemistry, Teknikringen 30, S-10044, Stockholm, Sweden.

Chemical Communications (Cambridge, England)

|December 6, 2008

Summary

This summary is machine-generated.

Disulfides and phosphines react to create a reversible disulfide metathesis. This process allows for dynamic bond exchange in disulfide chemistry.

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Area of Science:

Chemistry
Organic Chemistry
Biochemistry

Background:

Disulfide bonds are crucial in protein structure and stability.
Controlling disulfide bond dynamics is essential for various chemical applications.

Purpose of the Study:

To investigate the reaction between disulfides and phosphines.
To establish a reversible disulfide metathesis process.

Main Methods:

Reaction of various disulfide compounds with different phosphine reagents.
Monitoring reaction progress using spectroscopic techniques.

Main Results:

The reaction between disulfides and phosphines was found to be reversible.
A disulfide metathesis process was successfully generated, enabling dynamic disulfide bond exchange.

Conclusions:

Phosphine-mediated disulfide metathesis offers a novel approach for manipulating disulfide bonds.
This methodology has potential applications in areas requiring dynamic covalent chemistry.