Polycyclic Aromatic Ketones – A Crystallographic and Theoretical Study of Acetyl Anthracenes

Reversible Friedel–Crafts acyl rearrangements of planar polycyclic aromatic ketones: dibenzofluorenones

“…The relative stabilities of dibenzouorenones, their Oprotonates and s-complexes are governed by a combination of steric and electronic effects. The reversible pathway of the Friedel-Cras acyl rearrangements (Agranat-Gore rearrangement 18,20,26 ) of dibenzouorenones established in the present study indicates that non-planarity is not a sine qua non condition for the rearrangements. In this case, thermodynamic control wins out over kinetic control, in contrast to the Friedel-Cras acyl rearrangements in the diacetylanthracene series.…”

“…25 The conformational variations in these PAKs, which contribute to the understanding of the motifs of reversibility, have been described. 26 We report here the results of experimental and theoretical study of the intramolecular Friedel-Cras acyl rearrangements of dibenzouorenones in PPA. We highlight the reversibility characteristics and the preference of thermodynamic control in the acyl rearrangements of these planar PAKs and the relevance of the notions of aromaticity/antiaromaticity herein.…”