Pyrenes undergo initial electrophilic substitution in the 1 position; a second substitution typically occurs in the 3, 6, or 8 positions. We sought a pyrene with synthetically useful handles in the unusual 2, 7 substitution pattern. To that end, 7-amino-2-pyrenecarboxylic acid was prepared by partial reduction of pyrene to 4, 5, 9, 10-tetrahydropyrene, Friedel- Crafts acylation in the 2 position, and conversion to 2-carbethoxytetrahydropyrene through ...
