Amination of a chlorosilane; N-tert-butyl-1,1-dimethyl-1-(2,3,4,5-tetramethylcyclopenta-2,4-dienyl)silanamine
SyntheticPage 669
DOI:
10.1039/SP669
Submitted Jul 26, 2013, published Jul 30, 2013
Chemicals Used
Chlorodimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dienyl)silane (Prepared in house, see page
668)
tert-butylamine (Aldrich)
Procedure
Cp†HSiMe2Cl (1.01 g, 4.70 mmol) was charged into a Schlenk vessel and dissolved in THF (25 ml). tert-Butylamine (1.18 ml, 0.82 g, 11.0 mmol, 2.5 eq.) was added and the solution stirred overnight. The solvent and unreacted tert-butylamine were removed in vacuo. Pentane (20 ml) was added and the solution filtered via cannula. The solvent was removed in vacuo to give a yellow oil (1.24 g, 95 %).
Author's Comments
Removal of THF works best if co-evaporated with pentane.
This is a classic Bercaw CpSiNR ligand for synthesis of CGC catalysts.
Data
1H NMR (400 MHz, C6D6): ö 2.65 (1H, s, Cp†H), 1.90 (6H, s, C2Me2), 1.73 (6H, s, CC2Me2), 0.97 (9H, s, tBu), 0.3 (1H, s, broad, NH), 0.0 (6H, s, SiMe2).
Lead Reference
P. Nickias, D. Devore and D. Wilson, WO9308199, 1993.
Supplementary Information
1H NMR (1H NMR.jcamp)
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Keywords: amination, amines, silyl amine, silyl chloride, substitution
