McMurry cyclisation of 1,n-bis(5-benzoyl-2-methoxyphenyl)alkanes 2 afforded 1,2-diphenyl[2.n]metacyclophan-1-enes 3, which were converted into the corresponding [n](4,5)phenanthrenophanes 5 by photo-induced cyclisation in the presence of iodine as an oxidant.
Medium-sized Cyclophanes. part 70: YamatoT., MiyamotoS., OkabeR., TazakiY., and AnaiH., J. Chem. Res., 2006, 493.
2.
(a) Op Het VeldP.H.G., and LaarhovenW.H., J. Am. Chem. Soc., 1977, 99, 7221; (b) R. Srinivasan, V.Y. Merrit, J.N.C. Hsu, P.H.G. Op Het Veld and W.H. Laarhoven, J. Org. Chem., 1978, 43, 980.
3.
MalloryF.B., and MalloryC.W., Org. React., 1984, 30, 1.
4.
(a) ArmstrongR.N., AmmonH.L., and DarnowJ.N., J. Am. Chem. Soc., 1987, 109, 2077; (b) S. Grimme, I. Pischel, M. Nieger and F. Vögtle, J. Chem. Soc., Perkin Trans. 2, 1996, 2771.
5.
(a) BlaschkeH., RameyC.E., CalderI., and BoekelheideV., J. Am. Chem. Soc., 1970, 92, 3675; (b) C.E. Ramey and V. Boekelheide, J. Am. Chem. Soc., 1970, 92, 3681.
6.
(a) MitchellR.H., and BoekelheideV., J. Am. Chem. Soc., 1974, 96, 1547; (b) Y.-H. Lai and H.-L. Eu, J. Chem. Soc. Perkin Trans. 1, 1993, 233.
7.
(a) MitchellR.H., VinodT.K., BodwellG.J., WeerawarnaK.S., AnkerW., WilliamsR.V., and BushnellG.W., Pure Appl. Chem., 1986, 58, 15; (b) Y.-H. Lai and S.-M. Lee, J. Org. Chem., 1988, 53, 4472; (c) G.J. Bodwell, J.N. Bridson, M.K. Cyrafiski, J.W. Kennedy, T.M. Krygowski, M.R. Mannion and D.O. Miller, J. Org. Chem., 2003, 68, 2089.
8.
(a) YamatoT., MatsumotoJ., TokuhisaK., SuehiroK., and TashiroM., Chem. Ber., 1992, 125, 2443; (b) T. Yamato, K. Fujita, K. Okuyama and H. Tsuzuki, New. J. Chem., 2000, 221.
9.
(a) YamatoT., TokuhisaK., and TsuzukiH., Can. J. Chem., 2000, 78, 1089; (b) T. Yamato, T. Furukawa, K. Tanaka and H. Tsuzuki, New J. Chem., 2002, 26, 1035; (c) T. Yamato, R. Okabe, M. Shigekuni and T. Furukawa, J. Chem. Res. (S), 2003, 608.
10.
GrützmacherH. -F., and NeumannE., Chem. Ber., 1993, 126, 1495.
11.
McMurryJ.E., Chem. Rev., 1989, 89, 1513.
12.
(a) Cyclophanes and eds. KeehnP.M., and RosenfieldS.M., Academic Press: New York, vols 1 and 2, 1983; (b) F. Vögtle, Cyclophane Chemistry, Wiley: Chichester, 1993.
13.
(a) YamatoT., FujitaK., FutatsukiK., and TsuzukiH., Can. J. Chem., 2000, 78, 1089; (b) T. Yamato, K. Fujita, T. Abe and H. Tsuzuki, New J. Chem., 2001, 25, 728; (c) T. Yamato, S. Miyamoto, T. Hironaka and Y. Miura, Org. Lett., 2005, 7, 3.
