Facile Photorearrangement of Some Crowded Azoxyarenes via Two Concurrent Pathways

Article abstract of DOI:10.1246/bcsj.61.3005

Naphthalene-1-ONN-azoxybenzenes and some unsymmetrically ortho-substituted ONN- and NNO-azoxybenzenes were prepared, and their photochemical behavior in ethanol was compared.The crowded azoxyarenes tend to undergo a facile Wallach rearrangement via the known azoxy-ortho oxygen migration and a concurrent pathway involving ONN-NNO-isomerization.The relative contribution of the two pathways was affected by substituents.