Reactions of acenaphthenequinone and aceanthrenequinone with arenes in superacid

The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF3SO3H (triflic acid), the condensation products are formed in good yields (58–99%, 10 examples) with high regioselectivity. Computational studies were also done to examine the structures and energies of mono- and diprotonated species from 6 and 7. The results from the condensation reactions are consistent with the formation of superelectrophilic species involving protosolvation of carboxonium ion intermediates.

Graphical abstractThe hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF3SO3H, the condensation products are formed in good yields (58–99%, 10 examples) with high regioselectivity. The results from the condensation reactions and also theoretical calculations are consistent with the formation of superelectrophilic species. Figure optionsDownload full-size imageDownload as PowerPoint slide