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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.

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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...

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Updated: Dec 11, 2025

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

Ynamide-Mediated Thionoester and Dithioester Syntheses.

Chaochao Yao¹, Jinhua Yang¹, Xiaobiao Lu¹

¹College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.

Organic Letters

|August 19, 2020

Summary

This summary is machine-generated.

A new ynamide-mediated synthesis efficiently produces thionoesters and dithioesters. This method utilizes selective addition and transesterification, offering a versatile approach for synthesizing these sulfur-containing compounds.

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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

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Published on: August 20, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Thionoesters and dithioesters are important sulfur-containing organic compounds.
Existing synthetic methods may have limitations in scope or efficiency.

Purpose of the Study:

To develop a novel and efficient synthetic route for thionoesters and dithioesters.
To explore the utility of ynamide-mediated reactions in sulfur chemistry.

Main Methods:

Selective addition of monothiocarboxylic acids to ynamides.
Transesterification of the resulting α-thioacyloxyenamides with nucleophilic -OH or -SH species.

Main Results:

Successful synthesis of various thionoesters and dithioesters.
Demonstrated broad substrate scope and excellent yields.
Mild reaction conditions were employed.

Conclusions:

The ynamide-mediated approach provides an attractive and efficient method for synthesizing thionoesters and dithioesters.
This novel strategy expands the synthetic toolbox for accessing valuable sulfur-containing compounds.