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DOI: 10.1039/A803481H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1893-1900

Laticyclic conjugated double bonds within the framework of oligocondensed bicyclo[2.2.2]octenes

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Wolfram Grimme, Jens Wortmann, Dirk Frowein, Johann Lex, Grace Chen and Rolf Gleiter

Abstract

The all-syn oligocondensed bicyclo[2.2.2]octenes 3, 5, 20 and 29 with two to five etheno bridges show interaction of their π-orbitals by σ-overlap. This laticyclic conjugation reveals itself in the PE and UV spectra of the series as well as in the site selectivity of the Diels–Alder reaction with inverse electron demand found for the dehydro derivatives 11 and 26. As shown in the crystal structures of 3, 5 and 20, the etheno bridges are positioned face to face at a distance which is smaller than the sum of their van der Waals radii.

References

  1. M. J. Goldstein and R. Hoffmann, J. Am. Chem. Soc., 1971, 93, 6193 CrossRef.
  2. H.-D. Martin and R. Schwesinger, Chem. Ber., 1974, 107, 3143 CAS.
  3. G. Sedelmeier, H. Prinzbach and H.-D. Martin, Chimia, 1979, 33, 329 CAS.
  4. J. Spanget-Larsen, R. Gleiter, G. Klein, C. W. Doecke and L. A. Paquette, Chem. Ber., 1980, 113, 2120 CAS.
  5. K. B. Wiberg, M. G. Matturro, P. J. Okarma and M. E. Jason, J. Am. Chem. Soc., 1984, 106, 2194 CrossRef CAS.
  6. H. Lange, W. Schäfer, R. Gleiter, P. Camps and S. Vazquez, J. Org. Chem., 1998, 63, 3478 CrossRef CAS.
  7. M. S. Raasch, J. Org. Chem., 1980, 45, 856 CrossRef CAS.
  8. J. Sauer and H. Wiest, Angew. Chem., Int. Ed. Engl., 1962, 1, 269 CrossRef.
  9. K. Alder and G. Stein, Chem. Ber., 1929, 62, 2337 Search PubMed.
  10. R. H. Shapiro, Org. React. (N.Y.), 1976, 23, 405 CAS.
  11. W. E. Truce and R. J. McManimie, J. Am. Chem. Soc., 1953, 75, 1672 CrossRef CAS.
  12. O. De Lucchi, V. Lucchini, L. Pasquato and G. Modena, J. Org. Chem., 1984, 49, 596 CrossRef CAS.
  13. (a) H. E. Zimmerman and R. M. Paufler, J. Am. Chem. Soc., 1960, 82, 1514 CrossRef CAS; (b) W. G. Dauben, G. T. Rivers, R. J. Twieg and W. T. Zimmerman, J. Org. Chem., 1976, 41, 887 CrossRef CAS; (c) C. Weitemeyer and A. de Meijere, Angew. Chem., Int. Ed. Engl., 1976, 15, 686 CrossRef; (d) S. Cossu, S. Battaggia and O. De Lucchi, J. Org. Chem., 1997, 62, 4162 CrossRef CAS.
  14. This synthesis of barrelene was developed by Andreas Kirst, Dissertation, University of Cologne, 1995.
  15. N. C. Yang, M.-J. Chen and P. Chen, J. Am. Chem. Soc., 1984, 106, 7310 CrossRef CAS.
  16. J. C. Carnahan and W. D. Closson, Tetrahedron Lett., 1972, 3447 CrossRef CAS.
  17. D. E. Paul, D. Lipkin and S. I. Weissman, J. Am. Chem. Soc., 1956, 78, 116 CrossRef CAS.
  18. (a) K. Mackenzie, J. Chem. Soc., 1965, 4646 RSC; (b) K. Mackenzie, J. A. K. Howard, R. Siedlecka, K. B. Astin, E. C. Gravett, C. Wilson, J. Cole, R. G. Gregory and A. S. Tomlins, J. Chem. Soc., Perkin Trans. 2, 1996, 1749 RSC; (c) K. Mackenzie, G. Proctor and D. J. Woodnutt, Tetrahedron, 1987, 43, 5981 CrossRef CAS.
  19. W. Grimme, K. Pohl, J. Wortmann and D. Frowein, Liebigs Ann., 1996, 1905 CAS.
  20. W. J. Hehre, L. Radom, P. v. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, USA, 1986 Search PubMed.
  21. GAUSSIAN94, Revision D.2: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakryewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzales and J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
  22. (a) N. H. March, Electron Density Theory of Atoms and Molecules, Academic Press, San Diego, CA, 1992 Search PubMed; (b) Density Functional Methods in Chemistry, eds. J. K. Labanowski and J. W. Andzelm, Springer-Verlag, New York, 1991 Search PubMed; (c) R. G. Parr and W. Yang, Functional Theory of Atoms and Molecules, Oxford University Press, New York, USA, 1989 Search PubMed.
  23. (a) A. D. Becke, Phys. Rev. A, 1986, 33, 2786 CrossRef CAS; (b) A. D. Becke, J. Chem. Phys., 1988, 88, 2547 CrossRef CAS; (c) C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785 CrossRef CAS.
  24. J. J. P. Stewart, J. Comput.-Aided Mol. Des., 1990, 4, 1 Search PubMed.
  25. T. Koopmans, Physica, 1934, 1, 104 Search PubMed.
  26. P. Bischof, J. A. Hashmall, E. Heilbronner and V. Hornung, Helv. Chim. Acta, 1969, 52, 1745 CrossRef CAS.
  27. (a) A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735 CrossRef CAS; (b) A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066 CrossRef CAS.
  28. A. Imamura and M. Ohsaku, Tetrahedron, 1981, 37, 2191 CrossRef CAS.
  29. (a) G. F. Woods and L. H. Schwartzman, J. Am. Chem. Soc., 1949, 71, 1396 CAS; (b) G. F. Woods and L. H. Schwartzman, J. Am. Chem. Soc., 1948, 70, 3394 CAS.
  30. SHELXL-93 Program for the refinement of crystal structures by G. M. Sheldrick, University of Göttingen, Germany, 1993.
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