Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Characterization of a Longicyclic (2,2,2,2) Conjugated π System in 1,4-Difluorobenzene–Naphthalene Biplanemer
Hideki OkamotoKyosuke SatakeMasaru Kimura
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1995 Volume 68 Issue 12 Pages 3557-3562

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Abstract

The electronic absorption spectrum 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 π 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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© 1995 The Chemical Society of Japan
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