Reactions of trimethylsilyl cyanide and N-(trimethylsilyl)diphenylmethyleneamine with nitrones and thermal decompositions of their adducts.
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概要
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Trimethylsilyl cyanide (<B>1</B>) and <I>N</I>-(trimethylsilyl)diphenylmethyleneamine (<B>2</B>) reacted with α-aryl-<I>N</I>-phenyl-nitrones to afford the corresponding 1: 1 adducts <B>4</B> and <B>5</B> respectively. Thermal decomposition of <B>4</B> in refluxing xylene gave azoxybenzene, stereoisomers of 2,3-diarylsuccinonitriles, α-iminonitriles and/or benzanilides, whose yields depended on the nature of substituents on phenyl group of <B>4</B>. On heating in benzene <B>5</B> afforded a mixture of azoxybenzene and <I>meso</I>-<I>N</I>,<I>N</I>′-bis(diphenylmethylene)-1,2-diarylethylenediamines. On the other hand, reactions of <B>1</B> and <B>2</B> with <I>N</I>-(diphenylmethylene)aniline <I>N</I>-oxide or <I>N</I>-(9-fluorenylidene)aniline <I>N</I>-oxide did not give the corresponding 1: 1 adducts, but instead compounds arising from thermal decomposition of initial 1: 1 adducts were directly obtained. The reaction of <B>1</B> with <I>N</I>-(<I>p</I>-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.
- 公益社団法人 日本化学会の論文
著者
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Tsuge Otohiko
Research Institute of Industrial Science, Kyushu University 86
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Tsuge Otohiko
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Urano Satoshi
Research Institute of Industrial Science, Kyushu University 86
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Iwasaki Takahiko
Research Institute of Industrial Science, Kyushu University 86
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