Skeletal transformations of perfluoro-1-phenylindan under the action of antimony pentafluoride

Perfluoro-1-phenylindan (1) was obtained from perfluoroindan and pentafluorobenzene in the presence of SbF5. Compound 1 heated with antimony pentafluoride at 170°C and then treated with water gave a mixture of perfluorinated 9-methylfluorene (5), 9-hydroxy-9-methylfluorene (6), 9-methyl-1,2,3,4,5,6,7,8-octahydroanthracene (7), 1,9-dimethyl-5,6,7,8-tetrahydro-β-naphthindan (8). When heated with SbF5 in the presence of HF and then treated with water, compound 1 is transformed to a mixture of products 5, 6, perfluoro-1,2,3,4,5,6,7,8-octahydroanthracene (9), perfluoro-10-methyl-9(10H)anthracenone (10) and 10-H-perfluoro-10-methyl-9(10H)anthracenone (11).