Octafluoro-9-fluorenone (2) is obtained by reaction of 2-bromooctafluorobiphenyl-2'- carboxylic acid (4) with n-butyllithium. The reaction illustrates an unusual intramolecular nucleophilic arylation involving attack at a carboxylate salt. Catalytic reduction gives octafluoro-9-fluorenol, rather than octafluorofluorene (1). 1 is synthesized by a six-step procedure from 2-bromononafluorobiphenyl (7). The key step involves an intramolecular ...
