Indirect electrolytic oxidation of thioamides using organotellurium as a mediator.
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概要
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Bis(<I>p</I>-methoxyphenyl) telluride (<B>1</B>) electrochemically reacted with supporting electrolytes such as tetrabutylammonium acetate and tetraethylammonium tosylate under anhydrous conditions to give tellurium(IV) diacetate <B>2a</B> and ditosylate <B>2b</B>, respectively. On the other hand, <B>1</B> was electrolyzed in the presence of water to give telluroxide <B>3</B>. It has turned out that the tellurium compounds <B>2a</B> and <B>2b</B> like telluroxide <B>3</B> are mild oxidizing agents, but <B>2b</B> behaves differently in a reaction towards thioamide. Thus <B>2a</B> and <B>3</B> converted it into nitrile, while <B>2b</B> did it into 1,2,4-thiadiazole. An indirect electrolytic oxidation of thioamides with <B>1</B> as a mediator was examined under various conditions. As a result, nitriles or 1,2,4-thiadiazoles could be chemoselectively formed, depending on the intermediacy of <B>2a</B> or <B>3</B> as an active species for the former and <B>2b</B> for the latter.
- 公益社団法人 日本化学会の論文
著者
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Aso Yoshio
Department Of Applied Chemistry Faculty Of Engineering Hiroshima University
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Ogura Fumio
Department Of Applied Chemistry Faculty Of Engineering Hiroshima University
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Otsubo Tetsuo
Department Of Applied Chemistry Faculty Of Engineering Hiroshima University
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Hu Nan
Department of Applied Chemistry, Faculty of Engineering, Hiroshima University
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Matsuki Toshiaki
Department of Applied Chemistry, Faculty of Engineering, Hiroshima University
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