Preparation of oxepines during direct chemical synthesis and facile oxygen walk reactions of arene oxides: theoretical predictions and experimental evidence

Abstract

The synthesis of arene oxides and oxepines, and the unexpectedly facile rearrangement of a range of non-K- and bay-region arene oxides of polycyclic aromatic hydrocarbons to isolable isomeric oxepines via a photochemical oxygen walk pathway is reported; oxepine formation can be predicted from PMO calculations which indicate the associated loss of resonance energy during the oxygen walk process.