DEFLUORINATION OF HEXADECAFLUOROBICYCLO[4,4,0]DEC-1(6)-ENE - A FACILE SYNTHESIS OF PERFLUOROAROMATICS

Depending mainly on the polarity of the aprotic solvent used, defluorination of hexadecafluorobicyclo[4,4,0]dec-1(6)-ene (1) with activated zinc gave tetradecafluorobicyclo[4,4.0]dec-1(2),6(7)-diene (2), perfluorotetralin(3), decafluoro-1,2-dihydronaphthalene(4) and perfluoronaphthalene(5). In methanol, 2,7-dimethoxy-dodecafluorobicyclo[4,4,0]dec-1(2),6(7)-diene (6) was formed. These products were characterized by elemental analysis, IR, UV, 1H and 19F NMR. An electron transfer and then a radical intermediate seem to be involved in such defluorination reactions. © 1990.