Synthesis and reactivity of bis(triethoxysilyl)methane, tris(triethoxysilyl)methane and some derivatives1

Add time:08/30/2019    Source:sciencedirect.com

Syntheses of new poly(trifunctional-silyl)alkanes, which are potent coupling agents of hybrid organic–inorganic materials have been thoroughly examined. Optimization of the Benkeser reaction using chloroform, trichlorosilane and tri-n-butylamine (respective ratios 1:4.5:3) afforded bis(trichlorosilyl)methane isolated as bis(triethoxysilyl)methane after ethanolysis (overall yield 60%). With nine equivalents of trichlorosilane, tris(trichlorosilyl)methane is preferentially formed, isolated as tris(triethoxysilyl)methane (30% yield). C-Substituted bis(triethoxysilyl) methanes were obtained after metallation of the α-carbon and trapping experiments with the corresponding alkyl halides. In the case of tris(triethoxysilyl)carbanion, only MeI and Br2 were able to give the anticipated products. Unexpectedly, CO2 insertion afforded the stable ketene, [(EtO)3Si]2CCO.

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