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 (SCI-Expanded) identifier identifier


1-(11-Benzoyl-11-azatricyclo[,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-[,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.