| 词条 | Trimethylsilyl cyclopentadiene |
| 释义 |
| ImageFile = Trimethylsilyl cyclopentadiene.svg | ImageSize = 150px | ImageAlt = | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = | PubChem = | SMILES = }} |Section2={{Chembox Properties | C=8 | H=14 | Si=1 | Appearance = Colorless liquid | Density = 0.833 g/mL[1] | MeltingPt = | BoilingPtC = 138 to 140 | BoilingPt_ref = [1] | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} 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 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 SynthesisTrimethylsilyl cyclopentadiene is prepared by the reaction trimethylsilyl chloride (Me3SiCl) with sodium cyclopentadienide (NaC5H5):[4][5] (CH3)3SiCl + NaC5H5 → C5H5Si(CH3)3 + NaCl References1. ^1 {{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/257885?lang=en | publisher = Sigma-Aldrich | title = Trimethylsilyl cyclopentadiene}} 2. ^{{cite journal | doi = 10.1016/S0022-2860(00)00549-4 | title = 1H NMR observation of trimethylsilyl migration in gas phase 5-trimethylsilylcyclopentadiene | year = 2000 | last1 = Taha | first1 = A.N. | last2 = Moreno | first2 = P.O. | last3 = Lemaster | first3 = C.B. | last4 = Lemaster | first4 = C.L. | last5 = True | first5 = N.S. | journal = Journal of Molecular Structure | volume = 553 | pages = 37}} 3. ^{{Cite web|url=https://www.sigmaaldrich.com/catalog/product/aldrich/257885|title=Trimethylsilyl cyclopentadiene, mixture of isomers 257885|website=Sigma-Aldrich|access-date=2018-12-05}} 4. ^{{cite journal |author1=Seki, R. |author2=Komatsu, S. | year = 2011 | title = Preparation of (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes | journal = Jpn. Kokai Tokkyo Koh. }} 5. ^{{cite encyclopedia|title=5-(Trimethylsilyl)-1,3-cyclopentadiene|authors=Francisco Palacios, Jesús M. de los Santos|year=2014|doi=10.1002/047084289X.rn01739|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis}} 3 : Cyclopentadienes|Organosilicon compounds|Trimethylsilyl compounds |
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