A series of heterocyclic alcohols have been reacted in the Brønsted superacid, triflic acid (CF<sub>3</sub>SO<sub>3</sub>H), to generate superelectrophilic intermediates. These dicationic species undergo efficient Friedel-Crafts reactions with arene nucleophiles. Several systems also show novel rearrangements involving the carbocationic centers, including the first examples of dicationic non-classical carbocations. It is also shown that this chemistry can be used to functionalize polystyrene resins.

Generating dicationic electrophiles from heterocyclic alcohols and their use in Friedel-Crafts reactions

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