Trimethylsilyl cyclopentadiene
| |
| Identifiers | |
|---|---|
| Properties | |
| C8H14Si | |
| Molar mass | 138.285 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.833 g/mL[1] |
| Boiling point | 138 to 140 °C (280 to 284 °F; 411 to 413 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Trimethylsilyl cyclopentadiene is an organosilicon compound with the chemical formula C8H14Si. This colorless compound is a liquid at room temperature. It is commonly used in the synthesis of metal cyclopentadienyl complexes.
Trimethylsilyl cyclopentadiene has been of theoretical interest as an example of a molecule that undergoes rapid sigmatropic rearrangement. Observations of trimethylsilyl cyclopentadiene using gas phase NMR spectroscopy show that the protons on the ring are chemically equivalent, indicated by a single peak. This phenomenon, an example of fluxionality, is explained by the migration of the silyl group from carbon-to-carbon, thereby giving the appearance of equivalent CH signals.[2]
Synthesis
Trimethylsilyl cyclopentadiene is prepared by treating trimethylsilyl chloride (Me3SiCl) with sodium cyclopentadienide (NaC5H5) and distilling at 36 °C.[3]
- (CH3)3SiCl + NaC5H5 → C5H5Si(CH3)3 + NaCl
References
- ^ a b "Trimethylsilyl cyclopentadiene". Sigma-Aldrich.
- ^ Taha, A.N.; Moreno, P.O.; Lemaster, C.B.; Lemaster, C.L.; True, N.S. (2000). "1H NMR observation of trimethylsilyl migration in gas phase 5-trimethylsilylcyclopentadiene". Journal of Molecular Structure. 553: 37. doi:10.1016/S0022-2860(00)00549-4.
- ^ Seki, R.; Komatsu, S. (2011). "Preparation of (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes". Jpn. Kokai Tokkyo Koh.