A series of 3,4-disubstituted (4a, b) or 3,4-fused (4c-e) 1,1-di-fluorocyclopropabenzenes, including the very strained 1,1-difluoro-3,4-dihydro-1 H-cyclobuta[a]cyclopropa[d]benzene (4e) have been synthesized and characterized. Dissolution of these difluoro derivatives in fluorosulfonic acid affords the fluoro cations 3a–e. ¹H-, ¹⁹F-, and ¹³C-NMR data of the cations are reported and discussed with respect to those of the precursors.