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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.

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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,...

Structural Isomerism

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Radical Reactivity: Steric Effects

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Related Experiment Video

Updated: Apr 23, 2026

The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique

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Silylated Stannanes and Stannides.

Roland C Fischer¹, Christoph Marschner¹

¹Institut für Anorganische Chemie, Technische Universität Graz, Stremayrgasse 9, 8010 Graz, Austria.

Inorganic Chemistry

|April 22, 2026

Summary

This summary is machine-generated.

Researchers synthesized tris(trimethylsilyl)stannyl potassium for easy stannyl ligand introduction. Steric and electronic properties can be tuned by modifying silyl groups, enabling access to novel organotin compounds.

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Area of Science:

Organometallic Chemistry
Silicon-Tin Chemistry

Background:

Organotin compounds are versatile in synthesis.
Trisilylated stannyl ligands offer unique steric and electronic properties.
Potassium stannides are valuable synthetic intermediates.

Purpose of the Study:

To develop a convenient method for preparing tris(trimethylsilyl)stannyl potassium.
To explore the modification of steric and electronic properties of stannyl ligands.
To synthesize novel bulky stannides and 1,2-dimetalated compounds.

Main Methods:

Reaction of tetrakis(trimethylsilyl)stannane with potassium tert-butoxide.
Substitution of trimethylsilyl groups with bulkier triorganosilyl, methyl, or phenyl groups.
Further reaction of modified stannanes with potassium tert-butoxide.
NMR spectroscopy and X-ray crystallography for characterization.

Main Results:

Successful synthesis of tris(trimethylsilyl)stannyl potassium.
Demonstrated tunability of stannyl ligand properties through group substitution.
Access to sterically demanding potassium stannides and 1,2-dimetalated species.
Detailed electronic and structural characterization of synthesized compounds.

Conclusions:

Tris(trimethylsilyl)stannyl potassium is an effective precursor for introducing trisilylated stannyl ligands.
Systematic modification of stannyl ligands allows fine-tuning of their properties.
The developed methods provide access to a range of novel organotin compounds with potential applications in synthesis.