A series of trifluoromethyl-substitutued arenes were studied in their reactions with Brønsted superacids. The products from these reactions suggest the formation of reactive electrophiles, such as carbocations, acylium cations, or equivalent electrophilic species. As such, Friedel-Crafts type reactions occur between these species and arene nucleophiles. NMR studies were done and the results suggest the formation of an acyl group from the trifluoromethyl groups in superacid.
A series of heterocycle‐substituted acetophenones were prepared and reacted with the Brønsted superacid CF3SO3H (triflic acid=trifluoromethanesulfonic acid). Cyclodehydration provided aryl‐substituted imidazo[2,1‐a]isoquinolines and related products (28–85%, seven examples). A mechanism is proposed involving dicationic intermediates.
A series of functionalized aza-polycyclic aromatic compounds were prepared by a superacid-promoted ring closing and opening reaction cascade. A reaction mechanism is proposed, which involves reactive dicationic intermediates. A key step in the conversions involves ipso protonation of an aryl group and elimination of an alkyl phenyl group.
pounds. -The title compounds are obtained by a superacid-promoted ring-closing/ring-opening cascade proceeding via a series of dicationic intermediates. -(KETHE, A.; LI, A.; KLUMPP*, D. A.; Tetrahedron 68 (2012) 16, 3357-3360, http://dx.
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