Phenylsilane: Difference between revisions
m sp as per WP:SULF |
No edit summary |
||
| Line 42: | Line 42: | ||
The use of phenylsilane proceeds with retention of the configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines<ref>Weber, W. P. ''Silicon Reagents for Organic Synthesis''. Springer-Verlag: Berlin, 1983. ISBN 0387116753.</ref>. |
The use of phenylsilane proceeds with retention of the configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines<ref>Weber, W. P. ''Silicon Reagents for Organic Synthesis''. Springer-Verlag: Berlin, 1983. ISBN 0387116753.</ref>. |
||
Phenylsilane can also be combined with |
Phenylsilane can also be combined with cesium fluoride. In aprotic solvents, it becomes a nonnucleophilic hydride donor. Specifically, phenylsilane-caesium fluoride has been shown to reduce 4-oxazolium salts to 4-oxazolines. This reduction gives yields of 95%<ref>Fleck, T. J. ''Encyclopedia of Reagents for Organic Synthesis'' DOI 10.1002/047084289X.rp101</ref>. |
||
==References== |
==References== |
||
Revision as of 00:40, 1 April 2008
Phenylsilane, also known as silylbenzene, a colorless liquid, is one of the simplest organosilanes with the formula C6H5SiH3. It is structurally related to toluene, with a silyl group replacing the methyl group. Both of these compounds have similar densities and boiling points due to these similarities. Phenylsilane is soluble in organic solvents.
Synthesis and reactions
Phenylsilane is produced in two steps from Si(OEt)4. In the first step magnesium bromobenzene is added to form Ph-Si(OEt)3. The approach of using a magnesium-bromine reagent is called a Grignard reaction. Reduction of the resulting Ph-Si(OEt)3 product with LiAlH4 affords phenylsilane[1].
Ph-MgBr + Si(OEt)4 → Ph-Si(OEt)3 + MgBr(OEt)
4 Ph-Si(OEt)3 + 3 LiAlH4 → 4 Ph-SiH3 + 3 LiAl(OEt)4
Uses
Phenylsilane can be used to reduce tertiary phosphine oxides to the corresponding tertiary phosphine.
P(CH3)3O + PhSiH3 --> P(CH3)3 + PhSiH2OH
The use of phenylsilane proceeds with retention of the configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines[2].
Phenylsilane can also be combined with cesium fluoride. In aprotic solvents, it becomes a nonnucleophilic hydride donor. Specifically, phenylsilane-caesium fluoride has been shown to reduce 4-oxazolium salts to 4-oxazolines. This reduction gives yields of 95%[3].
References
- ^ Minge, O.; Mitzel, N. W.; and Schmidbaur, H. Synthetic Pathways to Hydrogen-Rich Polysilylated Arenes from Trialkoxysilanes and Other Precursors. Organometallics 2002, 21, 680-684. DOI 10.1021/om0108595.
- ^ Weber, W. P. Silicon Reagents for Organic Synthesis. Springer-Verlag: Berlin, 1983. ISBN 0387116753.
- ^ Fleck, T. J. Encyclopedia of Reagents for Organic Synthesis DOI 10.1002/047084289X.rp101