Advertisement

Quest for Higher Prismanes

  • Goverdhan Mehta
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

Prismanes are a fascinating class of (CH)2n polyhedranes of hb;h symmetry (Dnh ) whose synthetic appeal has been sustained through the prediction and expectancy of novel structural characteristics and unusual chemical reactivity. Among the prismanes, the current favourite for synthesis is [6]-prismane, the heptacyclic, face-to-face dimer of benzene of Dgh symmetry. In our quest for hexaprismane, a novel pentacyclic dimer of benzene and 1,4-bishomohexaprismane “Garudane” (face-to-face dimer of norbornadiene) have been identified as the two advanced precursors and their syntheses have been accomplished through novel strategies. Efforts directed towards the conversion of these precursors to [6]-prismane are described. Some experiments enroute to [7]-prismane and [8]-prismane have been explored.

Keywords

Methylene Blue Ring Expansion Ring Contraction Cyclobutane Ring Synthetic Appeal 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1. (a)
    V.I. Minkin, R.M. Minyaev, Zh. Org. Khim., 1981, 17, 221.Google Scholar
  2. 1. (b)
    N.L. Allinger, P.E. Eaton, Tetrahedron Lett., 1983, 3697.Google Scholar
  3. 1. (c)
    R.M. Martin, unpublished results quoted in ref. 4b.Google Scholar
  4. 1. (d)
    V.P. Reddy, E.D. Jemmis, Tetrahedron Lett., 1986, 3771.Google Scholar
  5. 1. (e)
    G. Mehta, S. Padma, E. Osawa, D.A. Barbiric, Y. Mochizuki, Tetrahedron Lett., 1987, 28, 1295.CrossRefGoogle Scholar
  6. 1. (f)
    G. Mehta, S. Padma, E.D. Jemmis, G. Leela, E. Osawa, D.A. Barbiric, Tetrahedron Lett., 1988, 29, 1613.CrossRefGoogle Scholar
  7. 1. (g)
    W.P. Dailey, Tetrahedron Lett., 1987, 47, 5787.CrossRefGoogle Scholar
  8. 1. (h)
    R. Engelke, P.J. Hay, D.A. Kleier, W.R. Wadt, J. Am. Chem. Soc., 1984, 106, 5439.CrossRefGoogle Scholar
  9. 1. (i)
    M.A. Miller, J.M. Schulman, J. Mol. Struct., 1988, 163, 133.Google Scholar
  10. 1. (j)
    R.L. Disch, J.M. Schulman, J. Am. Chem. Soc., 1988, 110, 2102.CrossRefGoogle Scholar
  11. 1. (k)
    E.D. Jemmis, J.M. Rudzinski, E. Osawa, Chem. Expres, 1988, 3, 109.Google Scholar
  12. 2.
    P.E. Eaton, T.R. Cole, J. Am. Chem. Soc., 1964, 86, 3157.CrossRefGoogle Scholar
  13. 3.
    T.J. Katz, N.J. Acton, ibid, 1973, 95, 2738.CrossRefGoogle Scholar
  14. 4. (a)
    P.E. Eaton, Y.S. Or, S.J. Branca, J. Am. Chem. Soc., 1981, 103, 2134.CrossRefGoogle Scholar
  15. 4. (b)
    P.E. Eaton, Y.S. Or, S.J. Branca, B.K.R. Shankar, Tetrahedron, 1986, 42, 1621.CrossRefGoogle Scholar
  16. 5. (a)
    P.E. Eaton, U.R. Chakraborty, J. Am. Chem. Soc., 1978, 100, 3634.CrossRefGoogle Scholar
  17. 5. (b)
    G. Mehta, A. Srikrishna, M.S. Nair, T.S. Cameron, W. Tacreiter, Ind. J. Chem., 1983, 22B, 621.Google Scholar
  18. 5. (c)
    H. Higuchi, K. Takatsu, T. Otsubo, Y. Sakata, S. Misumi, Tetrahedron Lett., 1982, 671.Google Scholar
  19. 5. (d)
    N.C. Yang, M.G. Horner, 1986, 543.Google Scholar
  20. 5. (e)
    V.T. Hoffmann, H. Musso, Angew. Chem. Int. Engl., 1987, 26, 1006.CrossRefGoogle Scholar
  21. 6.
    G. Mehta, S. Padma, J. Am. Chem. Soc., 1987, 109, 2212.CrossRefGoogle Scholar
  22. 7.
    G. Mehta, S. Padma, J. Am. Chem. Soc., 1987, 109, 7230.CrossRefGoogle Scholar
  23. 8.
    J.A. Marshall, G.L. Bundy, J. Am. Chem. Soc., 1966, 88, 4291.CrossRefGoogle Scholar
  24. 9.
    The protruding bridges (“wings”) in 8 are reminiscent of “Garuda” (Sanskrit), the mythological Hindu demi-god, part-bird, part-man, see: Encyclopaedia 3ritanica, Micropaedia 1981; Vol. IV, p.425. According to the von Baeyer system of nomenclature : heptacyclo- [9.3.0.02,5,03,13.04,8.06,10.09,,2]-tetradecane.Google Scholar
  25. 10.
    T.J. Chow, Y.S. Chao, L-K, Liu, J. Am. Chem. Soc., 1987, 109, 797 and previous references cited therein.CrossRefGoogle Scholar
  26. 11. (a)
    O. Diels, K. Alder, Chem. Ber., 1929, 62, 2337Google Scholar
  27. 11. (b)
    R.C. Cookson, R.R. Hill, J. Hudec, J. Chem. Soc., 1964, 3043.Google Scholar
  28. 12.
    L.C. Blaszczak, J.E. McMurry, J. Org. Chem., 1974, 39, 258.CrossRefGoogle Scholar
  29. 13.
    E. Osawa, D.A. Barbiric, O.S. Lee, Y. Kitano, S. Padma, G. Mehta, submitted for publication to J. Chem. Soc., Perkin Trans. II.Google Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Goverdhan Mehta
    • 1
  1. 1.School of ChemistryUniversity of HyderabadHyderabadIndia

Personalised recommendations