Bis([2.2]metacyclophane) bipyridinium was synthesized for the first time and it was found that this cyclophane compound was reduced at more negative potentials than the corresponding bipyridinium, having no cyclophane skeleton, due to a transannular CH–p interaction between the aromatic ring of the cyclophane and CH portion next to nitrogen atom.
TsugeA., IshiiT., SawadaT., MatakaS., and TashiroM., Chem. Lett., 1994, 1529.
11.
TsugeA., MoriguchiT., MatakaS., and TashiroM.J. Org. Chem., 1995, 60, 4930.
12.
TsugeA., MoriguchiT., MatakaS., and TashiroM.Liebigs Ann., 1996, 769.
13.
TsugeA., Nishimoto, UchidaM., YasutakeM., MoriguchiT., and SakataK., J. Org. Chem., 1999, 64, 7246.
14.
(a) HeyrovskyM., J. Chem. Soc., Chem. Commun., 1987, 1856.
15.
ImabayashiS.I., KitamuraN., TazukeS., and TokudaK., J. Electroanal. Chem., 1988, 243, 143.
16.
(a) NagamuraT., and SakaiK., J. Chem. Soc., Faraday Trans. 1, 1988, 84, 3529.
17.
NosakaY., and FoxM. A., J. Phys. Chem., 1988, 92, 1893.
18.
TashiroM., and YamatoT., J. Org. Chem., 1981, 48, 2313.
19.
TashiroM., ArimuraT., and YamatoT., Chem. Pharm. Bull., 1983, 31, 370.
20.
The semiempirical MO cakculation(PM3) were performed with MOPAC97 program.
21.
AsakawaM., AshtonP. R., BoydS. E., BrownC. L., GillardR. E., KocianO., RaymoF. M., StoddartJ. F., TolleyM. S., WhiteA. J. P., and WilliamsD. J., J. Org. Chem., 1997, 62, 26.