<jats:title>Abstract</jats:title>
<jats:p>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.</jats:p>