The isomeric perfluorinated didehydrobenzenes, ortho-, meta-, and para-didehydrobenzene, as well as various substituted meta-didehydrobenzene derivatives were generated and spectroscopically characterized in cryogenic matrices. Substituent effects on
geometric and electronic properties were analysed using quantum chemical calculations. The photochemical generation of a para-didehydrobenzene derivative by photo-Bergman reaction of a cyclic enediyne was also investigated by matrix isolation.
Tetrafluorophenylnitrene-4-yl, a quartet ground state nitrene radical, was synthesized by photolysis of tetrafluoroiodoazidobenzene and characterized by means of IR and ESR spectroscopy. Additionally the reactions of tetrafluorooxocyclohexadienylidene
with acetylene and the generation and photochemical rearrangement of tetrafluoro-para-xylylene were investigated using matrix isolation spectroscopy