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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.

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.

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, similar...

Sulfur Assimilation

Sulfur Assimilation

Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...

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.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Related Experiment Video

Updated: Jun 30, 2026

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

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

Published on: April 9, 2018

Controlled Sulfane Sulfur Delivery via Allyl Disulfide Rearrangement-Mediated Thiosulfoxide Formation.

Zhengyuan Jiang¹, William F Bancroft¹, Conrad N A Du¹

¹Department of Chemistry, Brown University, Providence, Rhode Island 02912, United States.

Journal of the American Chemical Society

|June 29, 2026

Summary

This study introduces thiosulfoxides as novel, stable donors for protein S-persulfidation, overcoming limitations of existing disulfide-based compounds. These new reagents enable controlled delivery of sulfane sulfur species for redox signaling research.

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Last Updated: Jun 30, 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

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Published on: May 20, 2019

Area of Science:

Biochemistry
Chemical Biology
Redox Signaling

Background:

Protein S-persulfidation is a crucial post-translational modification in redox signaling.
Hydropersulfides (RSSH) and hydrogen persulfide (H2S2) are key sulfane sulfur species but are highly reactive and unstable.
Existing disulfide-based donors for S-persulfidation suffer from limitations due to unavoidable disulfide exchange reactions with cellular thiols.

Purpose of the Study:

To explore thiosulfoxides as stable and controllable equivalents of RSSH/H2S2 for protein S-persulfidation.
To develop a new class of reagents for inducing protein S-persulfidation via a novel mechanism.
To investigate the utility of allyl disulfide rearrangements in generating reactive sulfane sulfur species.

Main Methods:

Studied spontaneous [2,3]-sigmatropic allyl disulfide rearrangements.
Identified structural elements influencing thiosulfoxide adduct formation.
Developed stable allyl disulfide reagents activated by cellular thiols.

Main Results:

Demonstrated that transient thiosulfoxide intermediates effectively transfer sulfane sulfur (S0) atoms.
Identified specific structural features that promote thiosulfoxide formation.
Developed stable allyl disulfide reagents (e.g., compound 3i) that induce protein S-persulfidation through a cascade mechanism.

Conclusions:

Thiosulfoxides represent a conceptually new approach for delivering reactive sulfane sulfur species.
The developed allyl disulfide reagents offer a stable and selectively activatable platform for inducing protein S-persulfidation.
This work provides a novel chemical tool for studying redox signaling pathways involving S-persulfidation.