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Synlett 2000; 2000(5): 0619-0622
DOI: 10.1055/s-2000-6632
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Cleavage of Arylalkylsilanes by Sodium Amide in Liquid Ammonia

Guang-Ri Sun* , Jin-Bao He, Hua-Jie Zhu, Charles U. Pittman, Jr.
  • *Department of Chemistry, University/Industry Chemical Research Center, Mississippi State University, Mississippi State, MS 39762 USA; Fax + 1-662-325-7611; E-mail: cpittman@ra.masstate.edu
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Publication Date:
31 December 2000 (online)

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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 were rapidly cleaved with little selectivity when the aryl groups had different substituents. The influence of metallic cations was important (NaNH2, KNH2 >> LiNH2 > Ca(NH2)2). Solvent and temperature were also studied.

cleavage - aryl C-Si bond - sodium amide - liquid ammonia