Unusual photorearrangement of 1,7-disubstituted 7-azabenzonorbornadiene

Altundas A., Tepe E., Akbulut N., Kara Y.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, cilt.45, sa.4, ss.613-616, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 4
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1134/s107042800904023x
  • Dergi Adı: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.613-616
  • Gazi Üniversitesi Adresli: Evet

Özet

1-(11-Benzoyl-11-azatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraen-1-yl)ethanone was synthesized by cycloaddition of 2-acetyl-N-benzoylpyrrole to benzyne. Direct photolysis of 1-(11-benzoyl-11-azatricyclo-[6.2.1.0(2,7)]undeca-2,4,6,9-tetraen-1-yl)ethanone in benzene gave N-(4-acetylnaphthalen-1-yl)benzamide. The formation of this product is discussed in terms of radical-stabilizing and destabilizing effect of electron-withdrawing group in the formation of cyclopropane ring.