有機ケイ素化合物の合成(第15報) : 2-Trimethylsilyl-p-benzoquinoneについて

概要

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A satisfactory result was obtained by a modified method for the synthesis of 2-trimethylsilyl-p-benzoquinone (I). Application of p-diazobenzenesulfonic acid to m- (VI) or o-(trimethylsilyl)phenol (VII) affords p-(2-trimethylsilyl-4-hydroxyphenylazo)-(VIII) or p-(3-trimethylsilyl-4-hydroxyphenylazo)-benzenesulfonic acid (X) which is reduced with sodium thiosulfate to 3-(IX) or 2-trimethylsilyl-4-aminophenol (XI). I is obtained in a good yield by the oxidation of IX or XI with dichromic acid. Addition reaction of I was then examined. I undergoes reaction with hydrochloric acid in methanol or with hydrogen chloride in chloroform to afford 2-chloro-p-hydroquinone. Refluxing of I with butylamine in methanol gives 2-butylamino-p-hydroquinone but I does not react with phenol. Reduction of I with sodium thiosulfate, hydroxylamine, or p-nitrophenylhydrazine affords 2-trimethylsilyl-p-hydroquinone (XIV) but I is not reduced by sulfur dioxide gas.
公益社団法人日本薬学会の論文
1967-05-25