Formation of Novel Polycyclic Aromatic Compounds by Scholl Reactions of Di(1-anthryl) Ketones via Cyclization and Rearrangement

Abstract The Scholl reactions of di(1-anthryl) ketones were performed with chloranil under an acidic condition. The reaction of the parent ketone gave a cyclized product containing a seven-membered ring, which was enantiomerically separable. In contrast, the reaction of 4-(mesityloxy)-1-anthryl derivative mainly afforded an unexpected polycyclic aromatic ketone consisting of eight six-membered rings via skeletal rearrangement. The structure and properties of these products and the reaction mechanism are reported.