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Silylation of potassium pentamethylcyclopentadienide; Trimethyl(1,2,3,4,5-pentamethylcyclopenta-2,4-dienyl)silane

SyntheticPage 653
DOI: 10.1039/SP653
Submitted Jul 24, 2013, published Jul 25, 2013
Alan D. Faulkner (alan.faulkner@warwick.ac.uk), Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: <IMG src="/images/empty.gif">Silylation of <SPAN id=csm1374770659286 class=csm-chemical-name title="potassium pentamethylcyclopentadienide" grpid="1">potassium pentamethylcyclopentadienide</SPAN><IMG src="/images/empty.gif">

Chemicals Used

KCp* (Prepared in house)
THF (Distilled over potassium)
Trimethylsilyl chloride (Aldrich)

Procedure

KCp* (1.0 g, 5.7 mmol) was suspended in THF (30 mL) and cooled to 0 °C. Trimethylsilyl chloride (0.74 mL, 7.6 mmol) was added drop wise and the resulting mixture was stirred overnight at room temperature. The resulting suspension was filtered through celite and the solvent was removed in vacuo to give the product as a yellow oil (Yield 0.79 g, 71 %).

Author's Comments

Caution! KCp* is very sensitive to air/moisture, take care handle in glovebox.
Celite is baked in oven for 24 h prior to use and filtration done through a Schlenk frit. 

Data

1H NMR (400 MHz, C6D6): δ 1.81 (12H, s, Ar-Me); 1.18 (3H, s br, Ar-Me); -0.09 (9H, s, Si-Me)

Lead Reference

Z. J. Tonzetich and R. Eisenberg, Inorg. Chim. Acta, 2003, 345, 340-344.
http://dx.doi.org/10.1016/S0020-1693(02)01276-8

Supplementary Information

Click to open interactive 1H NMR spectrum
1H NMR (1H NMR.jcamp)

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Get structure file (.cdx, .sk2, .mol)

Keywords: addition, aromatics/arenes, KCp*, Silylation