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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.

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.

Oxidation of Phenols to Quinones

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...

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.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

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Related Experiment Video

Updated: Apr 22, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

Published on: June 21, 2021

Visible-light-induced oxidant-free thiol-disulfide transformation.

Junhui Wang¹, Dandan Fan¹, Zhijie Li¹

¹College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, China.

Organic & Biomolecular Chemistry

|April 21, 2026

Summary

This study introduces a new, mild method for synthesizing disulfides using visible light and cerium catalysts. This approach avoids harsh oxidants and works well for complex molecules like peptides, offering greener chemical synthesis.

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Last Updated: Apr 22, 2026

Resin-Assisted Capture Coupled with Isobaric Tandem Mass Tag Labeling for Multiplexed Quantification of Protein Thiol Oxidation

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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

Area of Science:

Organic Chemistry
Catalysis
Green Chemistry

Background:

Disulfides are crucial in diverse fields like pharmaceuticals and materials science.
Conventional disulfide synthesis often uses transition metals and oxidants, causing environmental and practical issues.
Challenges include over-oxidation, low atom economy, and difficulties with complex molecules.

Purpose of the Study:

To develop a mild and efficient synthetic strategy for disulfide bond formation.
To avoid the use of transition metal catalysts and external oxidants.
To enable the modification of complex molecules, including peptides.

Main Methods:

Visible-light photoredox catalysis.
Dehydrogenative coupling catalyzed by cerium salts.
Application to various sulfur-containing substrates and peptides.

Main Results:

Successful synthesis of disulfides under mild conditions without added oxidants.
Demonstrated compatibility with thiophenols, thiols, and peptides.
Scalability of the reaction using microchannel continuous-flow technology.

Conclusions:

The proposed method offers a greener and more versatile alternative for disulfide synthesis.
Cerium-catalyzed visible-light coupling is effective for complex molecular structures.
The continuous-flow process indicates significant potential for industrial applications in chemical manufacturing.