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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.

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...

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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Updated: Apr 25, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Published on: April 10, 2015

Ruthenium-Catalyzed Synthesis of S,C-Sulfonium Ylides.

Qionglin Ge^1,2, Yaxi Liu^1,2, Zhiyue He^2,3

¹School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China.

The Journal of Organic Chemistry

|April 24, 2026

Summary

A new ruthenium-catalyzed reaction efficiently synthesizes S,C-sulfonium ylides from sulfides and iodonium ylides. This method offers broad substrate compatibility and functional group tolerance for diverse applications.

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Area of Science:

Organic Chemistry
Catalysis
Sulfonium Ylide Chemistry

Background:

Sulfonium ylides are versatile synthetic intermediates.
Existing methods for sulfonium ylide synthesis can be limited in scope or require harsh conditions.

Purpose of the Study:

To develop a novel and efficient method for synthesizing S,C-sulfonium ylides.
To expand the synthetic utility of sulfonium ylide chemistry.

Main Methods:

Ruthenium-catalyzed transylidation reaction.
Utilized sulfides and iodonium ylides as starting materials.
Mild reaction conditions were employed.

Main Results:

Achieved unprecedented synthesis of S,C-sulfonium ylides.
Demonstrated broad substrate compatibility and good functional group tolerance.
Successful scaled-up synthesis and transformation experiments.

Conclusions:

The developed ruthenium-catalyzed reaction provides an efficient route to structurally diverse sulfonium ylides.
This method significantly advances sulfonium ylide chemistry.
Highlights synthetic utility and potential for broader applications.