M. A. Cook, C. Eaborn, A. Jukes
Oct 1, 1970
Citations
0
Influential Citations
95
Citations
Quality indicators
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Tris(trimethylsilyl)methane readily undergoes metallation when treated with methyllithium in a mixture of tetrahydrofuran and diethyl ether, and the [tris(trimethylsilyl)methyllithium produced is remarkably stable in tetrahydrofuran. The ease of formation and the stability of the organolithium compound may be associated with stabilization of the carbanion (Me3Si)3C− by delocalization of the lone pair of electrons into the d-orbitals of the silicon atom. The organolithium compound can also be obtained by treatment of tris(trimethylsilyl)methyl chloride with lithium, methyllithium, or the n-butyllithiumN,N,N′,N′-tetramethylethylenediamine complex. It couples normally with the halides MeI, Me3SiCl, Me2HSiCl, Me3GeBr, and Me3SnCl, and gives the new acid (Me3Si)3CCO2H on carbonation.