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Persistent Dialkylsilanone Generated by Dehydrobromination of Dialkylbromosilanol
Shintaro Ishida1, Takashi Abe2, Fumiya Hirakawa2
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578 (Japan). sishida@m.tohoku.ac.jp.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 4, 2015
Summary
Researchers synthesized a stable dialkylsilanone at low temperatures. This persistent silicon compound undergoes unique reactions and isomerization, offering new insights into organosilicon chemistry.
Area of Science:
- Organosilicon Chemistry
- Synthetic Chemistry
Background:
- Dialkylsilanones are reactive intermediates in organosilicon chemistry.
- Understanding their stability and reactivity is crucial for developing new synthetic methodologies.
Purpose of the Study:
- To synthesize and characterize a persistent dialkylsilanone.
- To investigate the reactivity and thermal stability of the synthesized dialkylsilanone.
Main Methods:
- Dehydrobromination of a dialkylbromosilanol using tris(trimethylsilyl)silyl potassium at -80°C.
- Characterization by Nuclear Magnetic Resonance (NMR) and Infrared (IR) spectroscopy.
- Reactions with water and mesitonitrile oxide; thermal stability studies.
Main Results:
- Successful synthesis of a persistent dialkylsilanone characterized by a unique signal in Silicon-29 NMR spectroscopy at 128.7 ppm.
- The silanone reacted with water to form a silanediol and with mesitonitrile oxide to yield a [2+3] cycloadduct.
- The silanone exhibited stability below -80°C but underwent 1,3-silyl migration isomerization to a siloxysilene at higher temperatures.
Conclusions:
- A stable dialkylsilanone was synthesized and characterized, demonstrating its potential as a synthetic building block.
- The observed isomerization pathway provides novel insights into silicon migration reactions.
- This study expands the scope of accessible silicon compounds and their chemical transformations.
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