PERFLUORINATED STELLANES - THE SYNTHESIS OF PERFLUORINATED BISNORADAMANTANE - LONG-RANGE F-19 NMR VIRTUAL COUPLING

摘要

A three-step synthesis of perfluorinated bisnoradamantane, F-tricyclo[3.3.0.0(3,7)]octane, the smallest unsubstituted perfluorinated cage compound yet reported in the literature, is described. Oleum oxidation of adamantane to adamantane-2,6-dione followed by aerosol fluorination to F-adamantane-2,6-dione which is then photodecarbonylated in near-quantitative yields produces the perfluorinated stellane. F-19 NMR spectra of these perfluorinated cage compounds, which exhibit long-range fluorine-fluorine virtual coupling, are described. The highly symmetric F-bisnoradamantane structure results in a highly symmetrical splitting pattern which is readily interpretable. [References: 18]