Reaction of perfluorotetralin with 1,2,3,4-tetrafluorobenzene in SbF5 medium: The formation of polycyclic compounds with a new carbon framework

Interaction of perfluorotetralin with 1,2,3,4-tetrafluorobenzene (1 mol) in the presence of SbF5 at 50-55 degrees C gives, after treatment of the reaction mixture with HF-pyridine, perfluoro-1,2,3,10b-tetrahydrofluoranthene. When the reaction mixture was treated with water, perfluoro-5,6-dihydrofluoranthen-6a(4H)-ol was obtained. The reaction of perfluorotetralin with 2 moles of 1,2,3,4-tetrafluorobenzene leads, after treatment with H2O, to a mixture of perfluorinated 5,6-dihydrofluoranthen-6a(4H)-ol, 8,13-dihydro-7bH-8,13-methanobenzo[5,6]cyclohepta[1,2,3-jk]fluoren-7b-ol and 13-(2,3,4,5-tetrafluorophenyl)-perfluoro-8,13-dihydro-7bH-8,13-methanobenzo[5,6]cyclohepta[1,2,3-jk]fluoren-7b-ol. When 1-(2,3,4,5-tetrafluorophenyl)perfluorotetralin was dissolved in SbF5-SO2ClF, 1-(2,3,4,5-tetrafluorophenyl)perfluoro-1-tetralinyl cation was generated. The latter undergoes cyclization at ambient temperature to form perfluoro-1,2,3,10b-tetrahydrofluoranthen-10b-yl cation, which was also generated from perfluoro-1,2,3,10b-tetrahydrofluoranthene in a separate experiment.

Automated summary

Research shows that the reaction of perfluorotetralin with various fluorinated benzenes can lead to the formation of different perfluorinated compounds, including perfluoro-1,2,3,10b-tetrahydrofluoranthene, perfluoro-5,6-dihydrofluoranthen-6a(4H)-ol, and others.