Klumpp Douglas A, Zhang Yiliang, Do Dat, Kartika Rendy
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois, 60115.
Appl Catal A Gen. 2008 Mar 1;336(1-2):128-132. doi: 10.1016/j.apcata.2007.08.036.
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.
研究了醋蒽醌（6）和苊醌（7）与一系列芳烃的羟烷基化反应。在与布朗斯特超强酸CF(3)SO(3)H（三氟甲磺酸）的反应中，缩合产物以良好的产率（58 - 99%，10个例子）和高区域选择性形成。还进行了计算研究，以检查6和7的单质子化和双质子化物种的结构和能量。缩合反应的结果与涉及羧鎓离子中间体质子溶剂化的超亲电物种的形成一致。
