Bulletin of the Chemical Society of Japan p. 3557 - 3562 (1995)
Update date:2022-08-16
Topics:
Okamoto, Hideki
Satake, Kyosuke
Kimura, Masaru
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.
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