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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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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Stable Silenolates and Brook-Type Silenes with Exocyclic Structures.

Michael Haas¹, Roland Fischer¹, Michaela Flock¹

¹Institute of Inorganic Chemistry and Institute for Chemistry and Technology of Materials, Graz University of Technology , Stremayrgasse 9, A-8010 Graz, Austria.

Organometallics

|November 18, 2014

Summary

Researchers synthesized novel exocyclic silenolates and silenes, discovering that aryl substitution influences reactivity and enables the isolation of a stable silene within a cyclopolysilane framework.

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Area of Science:

Organosilicon Chemistry
Synthetic Inorganic Chemistry
Materials Science

Background:

Cyclopolysilanes are a unique class of silicon compounds with diverse structural motifs.
Silenes, silicon analogs of alkenes, are typically reactive intermediates.
Exocyclic functionalization of silicon rings offers pathways to novel structures and properties.

Purpose of the Study:

To synthesize and characterize novel silenolates with exocyclic structures.
To investigate the influence of substituents on silenolate reactivity and silene character.
To synthesize and isolate stable exocyclic silenes incorporated into cyclopolysilane frameworks.

Main Methods:

Synthesis of silenolates via reaction of acylcyclohexasilanes with potassium tert-butoxide.
Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy.
Structural determination via single-crystal X-ray diffraction analysis.

Main Results:

Successful synthesis of the first silenolates with exocyclic structures: [(Me3Si)2Si(Si2Me4)2SiC(R)O]-K+.
Aryl-substituted silenolates (mesityl, o-tolyl) showed increased silene character compared to alkyl (1-adamantyl) derivatives.
Isolation and characterization of a stable exocyclic silene, (Me3Si)2Si(Si2Me4)2Si=C(OSiiPr3)Mes, featuring an sp2 silicon atom in a cyclopolysilane ring.

Conclusions:

The coordination of the potassium counterion plays a crucial role in the electronic properties of exocyclic silenolates.
Aryl substituents promote the formation of functionalized silenes, while alkyl substituents lead to silylated products.
This study reports the first stable, isolated silene integrated into a cyclopolysilane ring system, opening new avenues in silicon chemistry.