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Note | Regular issue | Vol 51, No. 1, 1999, pp.141-144
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8318
Photochemistries of Oxadiazabicyclo[1.2.4]nonadiene, Oxadiazabicyclo[2.2.3]nonadiene, and Oxatriazabicyclo[2.2.3]nonadiene Systems: Cycloreversion Reactions to Generate Azepine or Diazepine Derivatives and Isomerization Reaction of Oxadiazabicyclo[2.2.3]nonadiene Systme to Oxadiazabicyclo[1.2.4]nonadiene System

Tsunetaka Tomita, Hiroyuki Ishiguro, and Katsuhiro Saito*

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


An irradiation of an oxadiazabicyclo[1.2.4]nonadiene derivative in acetonitrile with a low pressure mercury lamp afforded an 1H-azepine derivative. An irradiation of an oxadiazabicyclo[2.2.3]nonacliene derivative gave an oxadiazabicyclo[1.2.4]nonadiene derivative and an 1H-azepine derivative. On the other hand, a photo-reaction of an oxatriaza-bicyclo [2.2.3]nonadiene derivative generated a 1H-1,2-diazepine derivative. All these reactions are considered to proceed through the same type of reaction intermediate.