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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side chains...

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Updated: Jul 20, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

A stable bicyclic compound with two Si=Si double bonds.

T Iwamoto¹, M Tamura, C Kabuto

¹Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan.

Science (New York, N.Y.)

|October 20, 2000

Summary

Researchers synthesized a silicon analog of spiropentadiene, a unique double-ring compound. This discovery challenges previous assumptions about silicon double bond accessibility and synthesis.

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Fabrication and Optimization of Type II Silicon Clathrate Films

Fabrication and Optimization of Type II Silicon Clathrate Films

Published on: October 14, 2025

Area of Science:

Organosilicon chemistry
Synthetic inorganic chemistry

Background:

Carbon readily forms double bonds, unlike silicon.
Silicon-silicon double bonds typically require bulky substituents for stabilization.

Purpose of the Study:

To synthesize and characterize a silicon analog of spiropentadiene.
To investigate the structural and electronic properties of silicon-silicon double bonds in a novel cyclic system.

Main Methods:

Isolation and purification of tetrakis[tri(t-butyldimethylsilyl)silyl]spiropentasiladiene.
X-ray crystallography to determine molecular structure.
Spectroscopic analysis (e.g., NMR, UV-Vis) to probe electronic interactions.

Main Results:

Successful isolation of a stable silicon analog of spiropentadiene.
Observed significant deviation from planarity in the double-ring structure.
Spectroscopic data revealed electronic interactions between silicon-silicon double bonds.

Conclusions:

Silicon-silicon double bonds can be stabilized in complex ring systems.
The synthesis of such compounds is more feasible than previously thought.
This work opens new avenues for organosilicon compound research.