Cleavage of arylalkylsilanes by sodium amide in liquid ammonia

The aryl carbon-silicon bonds in arylalkyl monosilanes have been cleaved by sodium amide in liquid ammonia. Sub-stoichiometric amounts of amide effect complete cleavage of the aryl anion. Reactions were complete in just a few minutes at room temperature except when bulky alkyl groups are present (eg . triisopropylphenylsilane). In dialkyldiarylsilanes both aryl functions we re rapidly cleaved with little selectivity when the aryl groups had differe nt substituents. The influence of metallic cations was important (NaNH4 KNH 2 much greater than LiNH2 > Ca(NH2)(2)). Solvent and temperature were also studied.