R. West, G. Gornowicz
Apr 1, 1971
Citations
0
Influential Citations
34
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract tert-Butyllithium/ N , N , N′ , N′ -tetramethylethylenediamine (TMEDA) complex reacts with trimethylchloro- and trimethylbromosilanes to give mixtures of the coupling product tert-butyltrimethylsilane (I) and metalation products 1-chloro-1,1,3,3,3-pentamethyldisilmethylene (II) and 1-bromo-1,1,3,3,3-pentamethyldisilmelene, respectively. Trimethylfluorosilane and tert-butyllithium/TMEDA give only (I). Compound (I) is also the major product when methoxytrimethylsilane is treated with tert-butyllithium/TMEDA, but ethoxytrimethylsilane gives predominantly the metalation product 1-ethoxy-1,1,3,3,3-pentamethyldisilmethylene (IV). Acetoxytrimethylsilane and tert-butyllithium/TMEDA give, ultimately, 2-(trimethylsiloxy)-3,3-dimethyl-1-butene (VII). Hexamethyldisiloxane is metalated by tert-butyllithium in pentane to give LiCH 2 SiMe 2 OSiMe 3 , which in the presence of TMEDA rearranges to give LiOSiMe 2 CH 2 SiMe 3 . The difunctional silanes, dimethyldichlorosilane and dimethyldiethoxysilane, react with tert-butyllithium/TMEDA complex to give only the coupling products tert-butyldimethylchlorosilane and tert-butyldimethylethoxysilane (VI).