title: Reactions of Acenaphthenequinone and Aceanthrenequinone with Arenes in Superacid.
abstract: The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF(3)SO(3)H (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.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois, 60115.
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
authors.forename: Yiliang
authors.initials: Y
authors.lastname: Zhang
authors.forename: Dat
authors.initials: D
authors.lastname: Do
authors.forename: Rendy
authors.initials: R
authors.lastname: Kartika