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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.

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Related Experiment Video

Updated: Jun 20, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Published on: January 3, 2018

Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides.

Jos J A G Kamps¹, Dong Zhang¹, Timothy D W Claridge¹

¹Chemistry Research Laboratory, Department of Chemistry and the Ineos Oxford Institute for Antimicrobial Research, University of Oxford Oxford OX1 3TA UK christopher.schofield@chem.ox.ac.uk.

RSC Medicinal Chemistry

|July 19, 2024

Summary

Rhodanine compounds can transform into enethiols, which are enzyme inhibitors. In DMSO, these enethiols dimerize into 1,3-dithiolanes and mixed disulfides, suggesting careful solvent selection for rhodanine research.

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Published on: August 1, 2018

Area of Science:

Medicinal Chemistry
Organic Chemistry
Biochemistry

Background:

Rhodanines are recognized as challenging for drug development, despite some applications in diabetes mellitus treatment and ongoing clinical trials.
Rhodanines can hydrolyze to form enethiols, known inhibitors of metallo-enzymes like metallo β-lactamases.

Purpose of the Study:

To investigate the chemical transformations of rhodanine-derived enethiols in dimethyl sulfoxide (DMSO).
To understand the potential for rhodanine and enethiol derivatives to yield multiple reaction products.

Main Methods:

Chemical characterization of rhodanine derivatives.
Analysis of reaction products formed in DMSO.

Main Results:

Rhodanine-derived enethiols were observed to dimerize in DMSO.
The dimerization products identified were 1,3-dithiolanes and mixed disulfides.
The study highlights the propensity of rhodanines and enethiols to form diverse products.

Conclusions:

Dimethyl sulfoxide (DMSO) should be used with caution as a storage solvent for rhodanines and enethiols due to potential dimerization.
Further research is warranted on the biological relevance of enethiols and their mixed disulfide derivatives.