190788-90-0Relevant academic research and scientific papers
Cationoid rearrangements in reactions of perfluoro-1-arylbenzocyclobutenes with antimony pentafluoride
Karpov, Victor M.,Mezhenkova, Tatyana V.,Platonov, Vyacheslav E.,Sinyakov, Vladimir R.
, p. 73 - 81 (2002)
In the presence of antimony pentafluoride at 130°C, the four-membered ring of perfluoro-1-(2-ethylphenyl)benzocyclobutene (2) undergoes cleavage, forming perfluoro-2-ethyl-2′-methyldiphenylmethane (5). Compound 5 is converted, under the action of SbF5 at 170°C, to perfluoro-8,9-dimethyl-1,2,3,4-tetrahydrofluorene (8). Perfluoro-1-(4-ethylphenyl)benzocyclobutene (3) remains unchanged at 130°C, whereas at 170°C it gives a mixture of perfluorinated 4′-ethyl-2-methyldiphenylmethane (9), 6-ethyl-1,2,3,4-tetrahydroanthracene (11) and 2-ethyl-9,10-dihydroanthracene (12). When heated with SbF5 at 170°C, perfluoro-1-phenylbenzocyclobutene (1) remains unchanged. Solution of compounds 2, 3, 5 and 9 in SbF5-SO2ClF generated the perfluorinated 1-(2-ethylphenyl)-1-benzocyclobutenyl (29), 1-(4-ethylphenyl)-1-benzocyclobutenyl (30), 2-ethyl-2′-methyldiphenylmethyl (31) and 4′-ethyl-2-methyldiphenylmethyl (32) cations, respectively.
