Trimethylsilyl cyclopentadiene

Trimethylsilyl cyclopentadiene is an organosilicon compound with the chemical formula C5H5Si(CH3)3. It exists as a colorless liquid. It is used in the synthesis of some metal cyclopentadienyl complexes and has attracted interest for its fluxional structure.

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).
Infobox references

Trimethylsilyl cyclopentadiene is 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]

Properties:[3]

refractive index n20/D 1.471(lit.)

bp 138-140 °C(lit.)

density 0.833 g/mL at 25 °C(lit.)

storage temp. −20 °C

Synthesis

Trimethylsilyl cyclopentadiene is prepared by the reaction trimethylsilyl chloride (Me3SiCl) with sodium cyclopentadienide (NaC5H5):[4][5]

(CH3)3SiCl + NaC5H5 → C5H5Si(CH3)3 + NaCl
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References
  1. "Trimethylsilyl cyclopentadiene". Sigma-Aldrich.
  2. 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.
  3. "Trimethylsilyl cyclopentadiene, mixture of isomers 257885". Sigma-Aldrich. Retrieved 2018-12-05.
  4. Seki, R.; Komatsu, S. (2011). "Preparation of (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes". Jpn. Kokai Tokkyo Koh.
  5. Francisco Palacios, Jesús M. de los Santos (2014). "5-(Trimethylsilyl)-1,3-cyclopentadiene". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01739.CS1 maint: uses authors parameter (link)
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