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)
Full Text: HTML
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.
Related Compounds
Related Articles:
Chiral synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1, 2: 5, 6-di-O-isopropylidene-. alpha.-D-glucofuranosyl)-9-boratabicyclo [3.3. 1] nonane. Brown HC, etal.
[J. Org. Chem. 53(6) , 1231-38, (1988)]