Preparation of [2.2]-para-, meta-, and ortho-cyclophanes containing a 1,3-cyclohexano group

(Note: The full text of this document is currently only available in the PDF Version )

Shaw-Tao Lin, Fu-May Yang and David W. Liang


Abstract

[2.2]-para-, meta-, and ortho-Cyclophanes containing a 1,3-cyclohexane ring bridged with two carbons were prepared through a coupling reaction to form dithiacyclophane, followed by oxidation to yield the sulfone and then pyrolysis.


References

  1. (a) F. N. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, 1991 Search PubMed; (b) F. Vogtle, Cyclophane Chemistry: Synthesis, Structures and Reactions, John Wiley & Sons, Chichester, 1993 Search PubMed; (c) V. V. Kane, W. H. de Wolf and F. Bickelhaupt, Tetrahedron, 1994, 50, 4575 CrossRef CAS; (d) R. Gleiter and M. Merger, Angew. Chem., Int. Ed. Engl., 1997, 36, 2427 CrossRef CAS.
  2. (a) F. M. Yang and S. T. Lin, J. Org. Chem., 1997, 62, 2727 CrossRef CAS; (b) H. Hopf, R. Savinsky, B. Diesselkamper, R. G. Daniels and A. de Meijere, J. Org. Chem., 1997, 62, 8941 CrossRef CAS.
  3. S. T. Lin, F. M. Yang and L. H. Lin, Tetrahedron, 1997, 53, 16133.
  4. T. Inukai and T. Kojima, J. Org. Chem., 1971, 36, 924 CrossRef CAS.
  5. N. G. Gaylord, Reduction with Complex Metal Hydrides, John Wiley & Sons, New York, 1956, pp. 391–531 Search PubMed.
  6. (a) A. C. Davies, Chem. Ind., 1977, 203 Search PubMed; (b) T. Yamato, K. Noda, K. Tokuhisa and M. Tashiro, J. Chem. Res. (S), 1994, 210 Search PubMed; P. N. Swepston, S. T. Lin, A. Hawkins, S. Humphrey, S. Siegel and A. W. Cordes, J. Org. Chem., 1981, 46, 3754 CrossRef CAS.
  7. (a) C. E. Johnson and F. A. Bovey, J. Chem. Phys., 1958, 29, 1012 CrossRef CAS; (b) Johnson and Bovey's ‘Table of Predicted Values of Shielding Contributions from Ring Currents in Aromatic Hydrocarbons’ is contained in Appendix B of J. W. Emsley, J. Feeney and L. H. Sutcliffe, High Resolution Nuclear Magnetic Resonance Spectroscopy, Pergamon Press, New York, 1965 Search PubMed.
  8. (a) L. A. Paquette, Org. React., 1977, 25, 1 CAS; (b) J. M. Clough, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 861 Search PubMed.
  9. (a) T. L. Chan, S. Fong, Y. Li, T. O. Man and C. D. Poon, J. Chem. Soc., Chem. Commun., 1994, 1771 RSC; (b) C. Y. Meyers, A. M. Malte and W. S. Matthews, J. Am. Chem. Soc., 1969, 91, 7510 CrossRef CAS.
  10. (a) W. F. Maier and P. v. R. Schleyer, J. Org. Chem., 1981, 103, 1891 CAS; (b) A. B. McEwen and P. v. R. Schleyer, J. Am. Chem. Soc., 1986, 108, 3951 CrossRef CAS.
  11. V. Boekelheide and T. A. Hylton, J. Org. Chem., 1973, 38, 3928 CrossRef CAS.
  12. (a) G. Bordwell, E. Ludger and R. Ludovica, Angew. Chem., Int. Ed. Engl., 1979, 18, 515 CrossRef; (b) S. A. Sherrod, R. L. D. Costa, R. A. Barnes and V. Boekelheide, J. Am. Chem. Soc., 1974, 96, 1565 CrossRef CAS.
  13. (a) I. Tabushi, H. Yamada, K. Matsushita, Z. Yoshida, H. Kuroda and R. Oda, Tetrahedron, 1972, 28, 3381 CrossRef CAS; (b) I. Tabushi and K. Yamamura, Top. Curr. Chem., 1983, 113, 145 CAS.
  14. (a) N. L. Allinger, Y. H. Yuh and J. Lii, J. Am. Chem. Soc., 1989, 111, 8551 CrossRef CAS; (b) N. L. Allinger, K. Chen, M. Rahamn and A. Pathiaseril, J. Am. Chem. Soc., 1991, 113, 4105.
  15. J. J. P. Stewart, Reviews in Computational Chemistry, eds. K. B. Lipkowitz and D. B. Boyd, VCH, New York, 1990, p. 45 Search PubMed.
  16. (a) R. H. Mitchell, T. K. Vinod and G. W. Bushnell, J. Am. Chem. Soc., 1990, 110, 3487 CrossRef; (b) R. H. Mitchell, T. K. Vinod and G. W. Bushnell, J. Am. Chem. Soc., 1985, 107, 3340 CrossRef CAS; (c) V. Boekelheide, Top. Curr. Chem., 1983, 113, 87 CAS; (d) F. Vogtle, Top. Curr. Chem., 1983, 115, 1; ibid., 1983, 113, 1 Search PubMed.
  17. (a) V. Boekelheide and R. A. Hollins, J. Am. Chem. Soc., 1973, 95, 3201 CrossRef CAS; (b) R. H. Mitchell, Org. Chem. (N.Y.), 1983, 45, 239 Search PubMed; (c) D. Kamp and V. Boekelheide, J. Org. Chem., 1978, 43, 3470 CrossRef CAS.
  18. (a) Y. Fukazawa, H. Kitayama, K. Yasuhara, K. Yohimuar and S. Usui, J. Org. Chem., 1995, 60, 1696 CrossRef CAS; (b) Y. H. Lai and T. H. Lim, J. Org. Chem., 1994, 59, 3381 CrossRef CAS; (c) H. F. Grutzmacher and E. Neumann, Chem. Ber., 1993, 126, 1495; (d) Y. H. Lai and H. T. Yap, J. Chem. Soc., Perkin Trans. 2, 1993, 703, 1373 RSC; (e) T. Wong, M. S. Yuen, T. C. Mark and H. N. Wong, J. Org. Chem., 1993, 58, 3118 CrossRef CAS; (f) Y. H. Lai and T. H. Lim, J. Org. Chem., 1989, 54, 642; (g) Y. H. Lai, J. Org. Chem., 1988, 53, 2360 CrossRef CAS.
  19. G. A. Haggis and L. N. Owen, J. Chem. Soc., 1953, 404 RSC.