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Communication | Regular issue | Vol 51, No. 8, 1999, pp.1775-1778
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8569
Photoreactions of N-Tosyldihydrodiazaazulanones to Form Diazaazulaones and Ionic Pairs between p-Toluenesulfonate Anion and Tropylium Ions

Tadayuki Doi, Hiroyuki Ishiguro, Michie Sato, and Katsuhiro Saito*

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


Low pressure mercury lamp irradiations of N-aryl-N’-tosyldthydrodiazaazulanones in acetonitrile afforded the corresponding N-aryldiazaazulanones. Analogous photoreactions but using tetrahydrofuran as a solvent gave ion pairs between p-toluenesulfonate (tosylate) anion and the corresponding tropylium ions. The reactions are conisidered to proceed via bond cleavage between the nitrogen atoms and the tosyl groups to form ionic intermediates, which leave tosylate anions and protons to form the diazaazulanone derivatives or give the ion pairs via hydrogen transfers.