Applied Catalysis A: General 2012-02-01

Reactions of Acenaphthenequinone and Aceanthrenequinone with Arenes in Superacid.

DouglasA Klumpp, Yiliang Zhang, Dat Do, Rendy Kartika

Index: Appl. Catal. A Gen. 336(1-2) , 128-132, (2008)

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Abstract

The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Br__nsted 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.