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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.

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Updated: Nov 26, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

One-Pot Four-Component Assembling for Selenoureas.

Lai Li¹, Jiaqi Wu¹, Linsha Wei¹

¹College of Chemistry and Materials Engineering, Wenzhou University, Chashan University Town, Wenzhou, Zhejiang Province 325035, People's Republic of China.

The Journal of Organic Chemistry

|December 10, 2020

Summary

This summary is machine-generated.

A new one-pot method efficiently synthesizes unsymmetrical selenoureas and cycloselenoureas using selenium powder and amines. This practical approach yields 33 novel compounds, including a potent fungicide.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Selenoureas are important sulfur analogs with diverse biological activities.
Efficient synthesis of unsymmetrical selenoureas remains a challenge.
Developing practical and mild synthetic routes is crucial for exploring their applications.

Purpose of the Study:

To develop a straightforward and efficient one-pot method for synthesizing unsymmetrical selenoureas and cycloselenoureas.
To explore the scope and limitations of the developed synthetic protocol.
To evaluate the potential biological activity of the synthesized compounds.

Main Methods:

Reaction of selenium powder, chloroform, and two different amines in the presence of a base.
One-pot synthesis under mild reaction conditions.
Purification and characterization of the synthesized selenourea and cycloselenourea derivatives.
Control experiments to identify key intermediates.

Main Results:

Successfully synthesized 33 new unsymmetrical selenoureas, including three chiral examples.
Synthesized eight new cycloselenoureas.
Demonstrated the practical, gram-scale synthesis of 1,1-Dimethyl-3-phenylselenourea, exhibiting good fungicidal activity.
Confirmed isoselenocyanate as a key intermediate in the reaction mechanism.

Conclusions:

The developed one-pot method provides an efficient and practical route to unsymmetrical selenoureas and cycloselenoureas.
The protocol is versatile, yielding a diverse range of novel compounds.
The synthesized 1,1-Dimethyl-3-phenylselenourea shows promising fungicidal properties, warranting further investigation.