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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.

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.

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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

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,...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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Related Experiment Video

Updated: May 5, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

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Published on: April 9, 2018

DABSO-based, three-component, one-pot sulfone synthesis.

Alex S Deeming¹, Claire J Russell, Alan J Hennessy

¹Department of Chemistry, University of Oxford, Chemistry Research Laboratory , Mansfield Road, Oxford OX1 3TA, United Kingdom.

Organic Letters

|December 7, 2013

Summary

This summary is machine-generated.

This study introduces a new method using DABSO, a sulfur dioxide surrogate, to create metal sulfinates from Grignard or organolithium reagents. These intermediates efficiently convert to sulfone products via reactions with various carbon electrophiles.

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Area of Science:

Organic Chemistry
Organometallic Chemistry

Background:

Sulfones are important functional groups in medicinal chemistry and materials science.
Efficient synthesis of sulfones often requires specialized reagents or harsh conditions.

Purpose of the Study:

To develop a novel and versatile method for synthesizing metal sulfinates.
To demonstrate the utility of these metal sulfinates in the preparation of diverse sulfone products.

Main Methods:

Reaction of Grignard or organolithium reagents with DABSO (a sulfur dioxide surrogate).
In situ trapping of generated metal sulfinates with various C-electrophiles.
Characterization of the resulting sulfone products.

Main Results:

Successful generation of diverse metal sulfinates using DABSO.
High yields of sulfone products obtained through trapping with alkyl, allyl, benzyl halides, epoxides, and (hetero)aryliodoniums.
Demonstration of the broad substrate scope and functional group tolerance.

Conclusions:

The use of DABSO provides a convenient route to metal sulfinates.
This method offers a versatile platform for the synthesis of a wide array of sulfone compounds.
The in situ trapping strategy simplifies the overall synthetic process.