Polycyclic fluoro-aromatic compounds. Part 9. Preparation and some reactions of decafluorofluoranthene

Abstract

Fluorinations of fluoranthene with cobalt trifluoride and potassium tetrafluorocobaltate give perfluoroperhydrofluoranthene and perfluorotetradecahydrofluoranthene, respectively. Defluorination of either of these over iron(II) oxide gives decafluorofluoranthene, which is attacked by nucleophiles (OMe^–, H^–, NH₂NH₂) at position 1, and then at 6, 3, and 4. Oxidation of decafluorofluoranthene with nitric acid gives octafluorofluoranthene-2,3-quinone and then heptafluoro-9-oxofluorene-1-carboxylic acid.