Unusual photorearrangement of 1,7-disubstituted 7-azabenzonorbornadiene


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

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol.45, no.4, pp.613-616, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 4
  • Publication Date: 2009
  • Doi Number: 10.1134/s107042800904023x
  • Title of Journal : RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.613-616

Abstract

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.