Studies of Acyl and Thioacyl Isocyanates. VIII. Cycloaddition Reactions of Benzoyl and Thiobenzoyl Isocyanates with Carbodiimides
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概要
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The investigations of cycloaddition reactions of benzoyl and thiobenzoyl isocyanates with carbodiimides have shown that the adducts formed from benzoyl isocyanates and <I>N</I>,<I>N</I>′-dicyclohexylcarbodiimide are the corresponding (4+2) cycloadducts, and not the (2+2) cycloadducts proposed by Neidlein. The reaction of isocyanates with <I>N</I>,<I>N</I>′-diphenylcarbodiimide at 0°C gave (2+2) cycloadducts, which were thermally isomerized into the corresponding (4+2) cycloadducts. Benzoyl isocyanates reacted with <I>N</I>-cyclohexyl-<I>N</I>′-phenylcarbodiimide to give (4+2) cycloadducts of isocyanates to the cyclohexyl-N=C bond in the carbodiimide. On treatment with neutral alumina, (4+2) cycloadducts were easily isomerized into 1,3,5-triazines. Thiobenzoyl isocyanate reacted with both the N=C bonds of the carbodiimide to afford two isomeric (4+2) cycloadducts. It has been found that benzoyl isocyanates reacted with <I>N</I>-phenyl-<I>N</I>′-<I>o</I>-tolylcarbodiimide to yield the corresponding (4+2) cycloadducts of isocyanates to the <I>o</I>-tolyl-N=C bond and/or the isomeric 1,3,5-oxadiazin-6-ones, depending on the nature of the substituent in the isocyanate. Reaction paths for the formation of the product are also discussed.
- 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, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Sakai Kazuko
Research Institute of Industrial Science, Kyushu University
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