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Acid-free Friedel–Crafts chemistry: A paradox? Nucleophilicity scales, based on reactions with benzhydrylium ions, show that many π systems are more nucleophilic than aqueous or alcoholic solutions that are generally employed as solvents for SN1 reactions. Solvolytically generated carbocations can, therefore, be trapped by donor-substituted arenes and alkenes to form products of Friedel–Crafts-type reactions in neutral aqueous solutions (see scheme).
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Hofmann et al. (2004) studied this question.
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