Trimethylsilyl cyclopentadiene
 | |
| Properties | |
|---|---|
| Molecular formula |
C8H14Si |
| Molar mass | 138.28 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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Trimethylsilyl cyclopentadiene is an organosilicon compound with the chemical formula C8H14Si. This colorless compound is a liquid at room temperature. The silicon atom makes a direct σ-bond with one of the carbons of the cyclopentadienyl group. Trimethylsilyl cyclopentadiene is commonly used as a starting material for the synthesis of metal cyclopentadienyl complexes.
Trimethylsilyl cyclopentadiene has the unique property of rapid sigmatropic rearrangement. Observations of trimethylsilyl cyclopentadiene using gas phase 1H NMR showed that the protons on the ring are chemically equivalent, causing a single peak. This phenomenon can be mostly attributed to the pi electrons of the cyclopentadiene interacting with vacant d-orbitals of the silicon atom. [2]
Synthesis
Pure 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
- ↑ 1.0 1.1 "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 fo (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes". Jpn. Kokai Tokkyo Koh.