The Analogy between Aromatic Bromination and the Cleavage of Trialkylarylsilanes by Bromine
The Analogy between Aromatic Bromination and the Cleavage of Trialkylarylsilanes by Bromine
复制标题
芳香族溴化与溴裂解三烷基芳基硅烷之间的类比
DOI：
10.1021/ja01634a014
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发表时间：
1954
期刊：
影响因子：
--
通讯作者：
A. Torkelson
中科院分区：
文献类型：
--
作者：
R. A. Benkeser;A. Torkelson
Five trimethylarylsilanes were cleaved with bromine. The following sequence, representing decreasing ease of cleavage was observed: 2-bromo-5-trimethylsilylthiophene> phenyltrimethylsilane> m-nitrophenyltrimethylsilane> p-nitro-phenyltrimethylsilane> o-nitrophenyltrimethylsilane. The reaction of phenyltrimethylsilane with bromine was found to exhibit over-all third-order kinetics (second order inbromine). The above data suggest a strong similarity between these silane cleavage reactions and aromatic bromination. By employing thisanalogy the stability of alkylarylsilanes toward halogen or any electrophilic reagent can be predicted by the application of aromatic orientation rules.
