Fluorocarbanion chemistry. Octafluorofluorene and companions

R Filler, AE Fiebig, MY Pelister

Index: Filler, Robert; Fiebig, August E.; Pelister, M. Yavuz Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1290 - 1295

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Citation Number: 17

Abstract

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 ...