Free accessResearch articleFirst published online 2003-1
Medium-Sized Cyclophanes,63. 1 Synthesis and Structure of [2.2]Metacyclophane-1,2-Diol and Conversion Into [2.2]Metacyclophane-1,2-Dione by Swern Oxidation
McMurry cyclisation of 1,2-bis(5-t-butyl-2-methyl-3-formylphenyl)ethane 2 afforded anti-[2.2]metacyclophan-1-ene 3 and anti-[2.2]metacyclophane-1,2-diols 4, which were converted into the corresponding 1,2-dione 6 by Swern oxidation.
Medium-sized Cyclophanes. part 62: YamatoT., FurukawaT., TanakaK., Ishi-iT., and TashiroM., Can. J. Chem., 2003, 81, 244.
2.
GriffinR.W.Jr., Chem. Rev., 1963, 63, 45.
3.
CramD.J., Acc. Chem. Res., 1971, 4, 204.
4.
BrownC.J., J. Chem. Soc., 1953, 3278.
5.
(a) AkaboriS., SatoT., and HataK., J. Org. Chem., 1968, 33, 3277; (b) T. Sato, S. Akabori, M. Kainosho and K. Hata, Bull. Chem. Soc. Jpn., 1966, 39, 856; (c) T. Sato, S. Akabori, M. Kainosho and K. Hata, Bull. Chem. Soc. Jpn., 1968, 41, 218; (d) R. W. Griffin, Jr., R. W. Baughman and C. E. Ramey, Tetrahedron Lett., 1968, 5419; (e) H. W. Gschwend, J. Am. Chem. Soc., 1972, 94, 8430; (f) W. S. Lindsey, P. Stokes, L. G. Humber and V. Boekelheide, J. Am. Chem. Soc., 1961, 83, 943; (g) B. H. Smith. Bridged Aromatic Compounds. Academic Press Inc., New York, N. Y., 1964.
6.
SinglerR.E., and CramD. J., J. Am. Chem. Soc., 1972, 94, 3512.
7.
TashiroM., and YamatoT., J. Org. Chem., 1982, 46, 1543.
8.
TashiroM., and YamatoT., J. Am. Chem. Soc., 1982, 104, 3701.
9.
(a) YamatoT., MatsumotoJ., IdeS., SuehiroK., KobayashiK., and TashiroM., Chem. Ber., 1993, 126, 447; (b) T. Yamato, M. Sato, K. Noda, J. Matsumoto and M. Tashiro, J. Chem. Research (S), 1993, 394; (M) 2601.
10.
YamatoT., FujitaK., IdeS., and NaganoY., J. Chem. Research (S), 1997, 190; (M) 1301.
11.
(a) McMurryJ.E., FlemingM. P., KeesK. L., and KrepskiL. R., J. Org. Chem., 1978, 43, 3255; (b) J. E. McMurry, Acc. Chem. Res., 1983, 16, 405; (c) J. E. McMurry, G. J. Haley, J. R. Matz, J. C. Clardy and G. V. Duyne, J. Am. Chem. Soc., 1984, 106, 5018; (d) J. E. McMurry, Chem. Rev., 1989, 89, 1513.
12.
MitchellR.H., and WeerawarnaS. A., Tetrahedron Lett., 1986, 27, 453.
HopfH., and MlynekC., J. Org. Chem., 1990, 55, 1361.
15.
GrützmacherH.-F., and NeumannE., Chem. Ber., 1993, 126, 1495.
16.
(a) TashiroM., and YamatoT., Synthesis, 1981, 435; (b) T. Yamato, J. Matsumoto, K. Tokuhisa, K. Tsuji, K. Suehiro and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1992, 2675; (c) T. Yamato, A. Miyazawa and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1993, 3127; (d) T. Yamato, Y. Saruwatari, L. K. Doamekpor, K. Hasegawa and M. Koike, Chem. Ber., 1993, 126, 2501.
17.
MancusoA.J., HuangS. L., and SwernD., J. Org. Chem., 1978, 43, 2480.
18.
TashiroM., YamatoT., and FukataG., J. Org. Chem., 1978, 43, 1413.
19.
RiecheA., GrossH., and HöftE., Chem. Ber., 1960, 93, 88.
20.
(a) TashiroM., YamatoT., and KobayashiK., J. Org. Chem., 1984, 49, 3380; (b) T. Yamato, J. Matsumoto, T. Ando, K. Tokuhisa and M. Tashiro, J. Chem. Research (S), 1991, 276.
21.
(a) VögtleF., and NeumannP., Angew. Chem., 1972, 84, 75; Angew. Chem. Int. Ed. Engl., 1972, 11, 73; (b) F. Vögtle and P. Neumann, Synthesis, 1973, 85; (c) F. Vögtle and G. Höhner, Top. Curr. Chem., 74, 1 (1978); (d) P. M. Keehn and S. M. Rosenfield, Cyclophanes, Academic Press, New York, 1983, vol. 1; (e) F. Vögtle, Cyclophane Chemistry, John Wiley & Sons Ltd., New York, 1993.
22.
(a) TashiroM., and YamatoT., J. Org. Chem., 1981, 46, 4556; (b) M. Tashiro and T. Yamato, J. Org. Chem., 1983, 48, 1461.
23.
YamatoT., FujitaK., AndoT., IdeS., NaganoY., and TashiroM., J. Chem. Research (S), 1996, 264; (M) 1434.
24.
(a) SingerR.E., and CramD. J., J. Am. Chem. Soc., 1971, 93, 4443; (b) D. J. Cram, R. B. Hornby, E. A. Truesdale, H. J. Reich, M. H. Delton and J. M. Cram, Tetrahedron, 1977, 30, 1757.