A Photochemical Route to Dibenzobarrelenes

Abstract

Dibenzobarrelenes have been prepared by the cycloaddition of benzyne to anthracenes. The first method gives complex mixtures from which only poor yields of 1, 4-adducts may be obtained,¹ exceot wgeb tetragakivebztbes are enokited,^2,3 Muller and Vergne have reported⁴ that dibenzobarrelene is formed by the reaction of acetylene with anthracene, but it may be significant that later workers have chosen to use either the above-mentioned benzyne route or a modification of the cycloaddition to anthracenne involving dichlorethylene followed by dechlorination to prepare the parent compound.⁵ Our approach to the synthesis of this ring system employs our previously described 1,2–photoaramatisation reactions.⁶ A significant feature of the present work is that it demonstrates that a photochemical reaction can be employed to generate compounds, in this case dibenzobarrelenes, known to be photolabile.⁷