Characterization of a Longicyclic (2,2,2,2) Conjugated ? System in 1,4-Difluorobenzene-Naphthalene Biplanemer

Article abstract of DOI:10.1246/bcsj.68.3557

The electronic absorption of a 1,4-difluorobenzene-naphthalene biplanemer 1 exhibited a characteristic absorption band around 290 nm.This was attributable to intramolecular charge transfer interaction between the longicyclic conjugated ? system and the benzene chromophore.The oxidation potential of 1 was 1.70 V (vs.Ag/AgCl), which was lower than those of the related compounds in which one of the double bonds of 1 was hydrogenated.Thermally, the biplanemer 1 underwent facile Cope rearrangement, followed by dehydrofluorination, to give 1-(4-fluorophenyl)naphthalene and 2-(3-fluorophenyl)naphthalene.