The thermal decomposition of N,O-diacyl-N-t-butylhydroxylamines. II. Thermal rearrangement of O-acyl-N-(2-(methylthio)-benzoyl)-N-t-butylhydroxylamines.
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概要
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Several <I>O</I>-acyl-<I>N</I>-[2-(methylthio)benzoyl]-<I>N</I>-<I>t</I>-butylhydroxylamines (<B>1</B>) were prepared and their thermal decompositions were studied. The thermal decomposition of <B>1</B> at 200 °C in <I>o</I>-dichlorobenzene gave <I>N</I>-<I>t</I>-butyl-2-(acyloxymethylthio)benzamide (<B>4</B>), the carboxylic acid derived from the acyl part of <B>1</B>, and 2-<I>t</I>-butyl-1,2-benzothiazol-3(2<I>H</I>)-one as the main products, together with small amounts of 4<I>H</I>-3,1-benzoxathiin-4-one, <I>N</I>-<I>t</I>-butyl-2-(methylthio)benzamide, methyl ester of the carboxylic acid, and <I>N</I>-<I>t</I>-butylamide. The benzamide (<B>4</B>) was found to be an initial product of the thermolysis and the subsequent decomposition gave the carboxylic acid and other products. Pummerer type reaction, <I>via</I> acylaminosulfonium ion as the intermediate, was suggested for the thermal decomposition of <B>1</B> since similar products were also obtained by the Pummerer reaction of <I>N</I>-<I>t</I>-butyl-2-(methylsulfinyl)benzamide with acylating reagents.
- 公益社団法人 日本化学会の論文
著者
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Kozuka Seizi
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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Uchida Yuzuru
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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Kobayashi Yusho
Department of Applied Chemistry, Osaka Institute of Technology
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