Silylation of potassium pentamethylcyclopentadienide
SyntheticPage 653
DOI:
Submitted: July 24, 2013, published: July 25, 2013
Authors
Alan D. Faulkner (alan.faulkner@warwick.ac.uk)
Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from

Chemicals
KCp* (Prepared in house)
THF (Distilled over potassium)
Trimethylsilyl chloride (Aldrich)
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.
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
http://dx.doi.org/10.1016/S0020-1693(02)01276-8
Supplementary Information
Keywords
addition, aromatics/arenes, KCp*, Silylation