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Trimethylsilyl cyclopentadiene

Chemical compound From Wikipedia, the free encyclopedia

Trimethylsilyl cyclopentadiene
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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.

Quick Facts Names, Identifiers ...

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

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Synthesis

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

(CH3)3SiCl + NaC5H5 → C5H5Si(CH3)3 + NaCl

References

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