The Reactions of Tris(Trimethylsilyl)Methyl Lithium with Some Epoxides

Tris(trimethylsilyl)methane, [(Me3Si)3CH] (1),could be metallated by use of methyllithium in tetrahydrofuran.Tris(trimethylsilyl)methyl lithium (TsiLi)(2) reacts with ethylene oxide and poly (GMA-co-EHMA) with the formation of a carbon-carbon bond. This method of preparing functionalised silanes is limited by the readiness with which TsiLi abstracts a proton, if one is available, rather than attack at carbon. In addition in the reaction with epoxides, the product alkoxide can transfer a silyl group from carbon to oxygen (5,6), however this was shown not to occur under the conditions of interest here. [TSiCH2CH2OH] (7) was halogenated (8,9) and estrificated (10-I), (I = 1-8) successively to the esteric and alkyl halide compounds.