Synthesis of imido-substituted 3,8-diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and their thermolysis.

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概要

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• Nucleophilic substitution of 4,7-dichloro-3,8-diphenyl-1,2-diazocine with succinimide, phthalimide, <I>N</I>-methyl-<I>p</I>-toluenesulfonamide, and <I>o</I>-benzosulfimide, in the presence of silver oxide, gave the corresponding 4-mono(imido)- and 4,7-di(imido)-1,2-diazocines. 4-Acetoxy-7-phthalimido- and 4-phenylthio-7-phthalimido-1,2-diazocine were also prepared. Thermolysis of the mono(imido)-1,2-diazocines in xylene under reflux afforded the corresponding di(imido)-1,2-diazocine and/or five pyridine derivatives, whose relative yields depended upon the nature of imido substitutents in the diazocines. However, 4,7-di(imido)-1,2-diazocines did not decompose in xylene under reflux. Thermolysis of 4,7-bis(phthalimido)-1,2-diazocine at 300–310 °C gave 3,6-bis(phthalimido)-2-phenylpyridine with the extrusion of benzonitrile. In the thermolysis of the acetoxy(230–240 °C) or phenylthio-substituted 1,2-diazocine (240–260 °C), 6-acetoxy- and 6-benzoyl-3-phthalimido-2-phenylpyridine, or 6(and 3)-phenylthio-3(and 6)-phthalimido-2-phenylpyridines were isolated together with benzonitrile, respectively. The feature of thermolysis was also discussed.

• 公益社団法人 日本化学会の論文

著者

• YOGI Seiichi

  Department of Chemistry, College of Science, University of the Ryukyus

• Tsuge Otohiko

  Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University

• Hokama Kozo

  Department of Chemistry, Faculty of Science and Engineering, Ryukyu University Naha

• Takayoshi Sadamori

  Department of Chemistry, Faculty of Science, Ryukyu University

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