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.

Superacid-Promoted Reactions of α-Ketoamides and Related Systems

“…The β-ketoamides are protonated at the two carbonyl oxygens in superacid, giving dicationic intermediates. A number of 1,2-dicarbonyl compounds have likewise been shown to form diprotonated superelectrophilic species in strongly acidic media . In this regard, we considered the possibility that the 1,2-dicarbonyl groups of α-ketoamides could form superelectrophiles capable of undergoing cyclizations to the aryl-substituted oxyindoles.…”

Characteristics of a novel photoinitiator aceanthrenequinone-initiated polymerization and cytocompatibility of its triggered polymer

“…Therefore, it is necessary to find and develop some photoinitiators having good photochemical properties and high polymerization efficiency with low toxicity, especially cytocompatibility and tissue compatibility. Aceanthrenequinone (AATQ) is early used in a variety of organic synthesis or as a chemical material intermediate [ [7] , [8] , [9] ], but no reports is, to date, involved in cytotoxicity and cytocompatibility of itself and its-initiated polymer on mammalian cells. Moreover, some studies have shown that AATQ is simultaneously a component of vehicle exhaust emissions and PM2.5 [ 10 , 11 ], suggesting that it could have potentially adverse effects on human body, but no toxicology parameters have been reported.…”

High-Tg Functional Aromatic Polymers

“…Depending on the acid strength and the nature of the carbonyl component monoprotonation, multiple protonation or only hydrogen-bond formation is possible. It is believed that α-diketones are diprotonated in the medium of superacids. ,,,− …”