Abstract
Vapour-phase ultraviolet irradiation of hexafluorobenzene in the presence of oxygen slowly yields hexafluoro-3-oxatricyclo[3.2.0.0 2,4]hept-6-ene ( 2) (10%). The CFCF bond in 2 adds (yields of adducts given) the dienes; cyclopentadiene (74%), furan (61%) and 2,5-diphenylisobenzofuran (59%); benzonitrile oxide (58%); chlorine (59%) and bromine (71%) photochemically. Heptene 2 isomerises thermally to hexafluorocyclohexa-2,4-dienone ( 6) (60%) at 50 °C, and reacts with diethyl ether at room temperature yielding ethylfluoride (89%) and 2-ethoxypentafluorocyclohexa-2,5-dienone (21%). The benzonitrile oxide adduct, upon flow pyrolysis at 440 °C, yields an isomeric oxepin derivative and the cyclohexadienone 6 with longer contact times. The chlorine adduct similarly yields a dichloro-oxepin derivative; attempts to dechlorinate this to hexafluoro-oxepin were unsuccessful. Benzonitrile oxide adds tone or both of the CC bonds of hexafluorobicyclo[2.2.0]hexa-2,5-diene; the 1:1 adduct isomerises thermally to the benzonitrile oxide-hexafluorobenzene adduct.
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