Free accessResearch articleFirst published online 2007-7
Medium-sized Cyclophanes. Part 76. 1 Synthesis of syn -9-methoxy (1,4)naphthaleno[3.3]metacyclophanes and their charge-transfer Complexes with Tetracyanoethylene in CH 2 Cl 2
The charge-transfer band of syn-9-methoxy(1,4)naphthaleno[3.3]metacyclophanes with tetracyanoethylene in CH2Cl2 are observed in the range of 604–606 nm, which is arising from the exclusive formation on the naphthalene ring due to the expanded π-electron density as well as the steric hindrance of the inner methoxy group at 9-position.
SaisyoT., ShiinoM., HironakaT., and YamatoT., J. Chem. Res., 2007, 141.
2.
ShinmyozuT., InazuT., and YoshinoT., Mem. Fac. Sci., Kyushu Univ., 1985, Ser. C 15, 79.
3.
ErnstL., Progress in Nuclear Magnetic Resonance Spectroscopy, 2000, 37, 47.
4.
(a) KeehnP.M., and RosenfieldS.M. (eds), Cyclophanes, Academic Press, New York, vols. 1&2, 1983; (b) F. Vögtle, Cyclophane-Chemistry, Wiley, Chichester, 1993.
5.
YamatoT., NodaK., and TanakaK., J. Chem. Res. (S), 2002, 63.
6.
YamatoT., OkabeR., SaisyoT., MiyamotoS., and MitazakiM., J. Chem. Res., 2006, 593.
7.
(a) TashiroM., and YamatoT., J. Org. Chem., 1981, 46, 4556; (b) M. Tashiro and T. Yamato, J. Org. Chem., 1983, 48, 1461; (c) T. Yamato, J. Matsumoto, S. Ide, K. Suehiro and M. Tashiro, Chem. Ber., 1993, 126, 447; (d) T. Yamato, K. Fujita and H. Tsuzuki, J. Chem. Soc. Perkin Trans. 1, 2001, 2089; (e) T. Yamato, K. Fujita, T. Abe and H. Tsuzuki, New J. Chem., 2001, 25, 728; (f) M. Takeshita and T. Yamato, Angew. Chem. Int. Ed., 2002, 41, 2156; (g) M. Takeshita and T. Yamato, Chem. Lett., 2004, 33, 844; (h) T. Yamato, S. Miyamoto, T. Hironaka and Y. Miura, Org. Lett., 2005, 7, 3.
8.
MerrifieldR.E., and PhillipsW.D., J. Am. Chem. Soc., 1958, 80, 2778.
9.
(a) CramD.J., and BauerR.H., J. Am. Chem. Soc., 1959, 81, 5971; (b) L.A. Singer and D.J. Cram, J. Am. Chem. Soc., 1963, 85, 1080; (c) M. Sheehan and D.J. Cram, J. Am. Chem. Soc., 1969, 91, 3553.
10.
KanedaT., and MisumiS., Bull. Chem. Soc. Jpn., 1977, 50, 3310.
11.
YamatoT., MatsumotoJ., ShinodaN., IdeS., ShigekuniM., and TashiroM., J. Chem. Res. (S), 1994, 178.
