Triethylsilane
Triethylsilane is the organosilicon compound with the formula (C2H5)3SiH. It is a trialkylsilane. The Si-H bond is reactive.
It was first discovered by Albert Ladenburg in 1872 among the products of reduction of tetraethyl orthosilicate with sodium and diethylzinc.[2] He also prepared it by a stepwise reduction via ethoxytriethylsilane and named it silicoheptyl hydride, reflecting the idea of a silicon compound analogous to a seven-carbon hydrocarbon.
This colorless liquid is used in organic synthesis as a reducing agent and as a precursor to silyl ethers.[3] As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.[4]
Additional reading
- Richard T. Beresis, Jason S. Solomon, Michael G. Yang, Nareshkumar F. Jain, and James S. Panek (1998). "Synthesis of Chiral (E)-Crotylsilanes: [3R- AND 3S-]-(4E)-Methyl 3-(Dimethylphenylsilyl)-4-Hexenoate ". Organic Syntheses. 75: 78
{{cite journal}}: CS1 maint: multiple names: authors list (link). - Alessandro Dondoni and Daniela Perrone (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2-[(4S)-N-tert-Butoxycarbonyl-2,2-Dimethyl-1,3,-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde ". Organic Syntheses. 77: 78.
- Pape C. (1881). "Über Siliziumpropylverbindungen". Ber. 14: 1873.
- Charles A. Kraus & Walter K. Nelson (1934). "The Chemistry of the Triethylsilicyl Group". J. Am. Chem. Soc. 56 (1): 195–202. doi:10.1021/ja01316a062.
References
- ^ a b c Sigma-Aldrich Co., Triethylsilane. Retrieved on 2015-01-30.
- ^ Ladenburg, A. (1872). "Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate". Justus Liebigs Annalen der Chemie (in German). 164 (2): 300–332. doi:10.1002/jlac.18721640212. ISSN 0075-4617.
- ^ Fry, James L.; Rahaim, Ronald J.; Maleczka, Robert E. (2007). "Triethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rt226.pub2. ISBN 978-0471936237.
- ^ Brookhart, M.; Grant, B. E. (1993). "Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway". Journal of the American Chemical Society. 115 (6): 2151–2156. doi:10.1021/ja00059a008.