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Silylation of potassium pentamethylcyclopentadienide

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Submitted: July 24, 2013, published: July 25, 2013

A contribution from 

Reaction Scheme

Chemicals

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 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

Keywords

addition, aromatics/arenes, KCp*, Silylation