A tetracationic electrophile has been generated in superacid and shown to undergo an arylation reaction with benzene. A cyclization product is also obtained in the absence of benzene, presumably from a tricationic intermediate. Using low-temperature NMR, the tetracationic species is directly observed from a FSOH-SbF-SOClF solution. Similar chemistry is described with a system involving penta- and tetracationic intermediates. These highly ionized structures and their chemistry were also examined by DFT calculation.
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