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DOI: 10.1039/A702911J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2269-2272

Towards a synthesis of C3-tribenzohemifullerene, a C42H18 fragment of [60]fullerene

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Goverdhan Mehta, Gautam Panda, Shailesh R. Shah and Ajit C. Kunwar

Abstract

A short, simple synthesis of C3-trinaphthotriphenylene 6, C42H24, from readily available precursors involving threefold Wittig reactions and threefold oxidative photocyclizations is reported; flash vacuum pyrolysis of 6 in the quest for C3-tribenzohemifullerene 5, C42H18, has so far led only to the formation of monobridged product 12, C42H22.

References

  1. (a) R. Faust, Angew. Chem., Int. Ed. Engl., 1995, 34, 1429 CrossRef CAS; (b) P. W. Rabideau and A. Sygula, Acc. Chem. Res., 1996, 29, 235 CrossRef CAS; (c) L. T. Scott, Pure Appl. Chem., 1996, 68, 291 CrossRef CAS; (d) G. Mehta and H. S. P. Rao, in Advances in Strain in Organic Chemistry, vol. 6, ed. B. Halton, JAI Press Inc., London, 1997 Search PubMed.
  2. (a) W. E. Barth and R. G. Lawton, J. Am. Chem. Soc., 1971, 93, 1730 CrossRef; (b) L. T. Scott, M. M. Hashemi, D. T. Meyer and H. B. Warren, J. Am. Chem. Soc., 1991, 113, 7082 CrossRef CAS; (c) A. Borchardt, A. Fuchiocello, K. V. Kilway, K. K. Baldridge and J. S. Siegel, J. Am. Chem. Soc., 1992, 114, 1921 CrossRef CAS; (d) G. Zimmermann, U. Nuecheter, S. Hagen and M. Nuechter, Tetrahedron Lett., 1994, 35, 4747 CrossRef; (e) C. Z. Liu and P. W. Rabideau, Tetrahedron Lett., 1996, 37, 3437 CrossRef CAS; (f) G. Mehta and G. Panda, Tetrahedron Lett., 1997, 38, 2145 CrossRef CAS.
  3. (a) A. H. Abdourazak, Z. Marcinow, A. Sygula, R. Sygula and P. W. Rabideau, J. Am. Chem. Soc., 1995, 117, 6410 CrossRef CAS; (b) S. Hagen, M. S. Bratcher, M. S. Erickson, G. Zimmermann and L. T. Scott, Angew. Chem., Int. Ed. Engl., 1997, 36, 406 CrossRef CAS.
  4. P. W. Rabideau, A. H. Abdourazak, H. E. Folsom, Z. Marcinow, A. Sygula and R. Sygula, J. Am. Chem. Soc., 1994, 116, 7891 CrossRef CAS.
  5. L. T. Scott, M. S. Bratcher and S. Hagen, J. Am. Chem. Soc., 1996, 118, 8743 CrossRef CAS.
  6. (a) G. Mehta, S. R. Shah and K. Ravikumar, J. Chem. Soc., Chem. Commun., 1993, 1006 RSC; (b) G. Mehta and K. Venkateswara Rao, Synlett, 1995, 317 CrossRef CAS; (c) G. Mehta, K. Venkateswara Rao and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1995, 1787 RSC; (d) G. Mehta, G. V. R. Sharma, M. A. Krishna Kumar, T. V. Vedavyasa and E. D. Jemmis, J. Chem. Soc., Perkin Trans. 1, 1995, 2529 RSC; (e) G. Mehta, G. Panda, R. D. Yadav and K. Ravikumar, Indian J. Chem. B, 1997, 301 CAS.
  7. Systematic IUPAC names: 6: naphtho[2,1-a]phenanthro[1,2-f]-picene; 10: 9-(1-naphthyl)benzo[rst]naphtho[2,1-a]pentaphene 11: (9R)-9-(1-naphthyl)-8,9-dihydrobenzo[rst]naphtho[2,1-a]pentaphene 12: acephenanthryleno[5,4,3-def]naphtho[2,1-a]picene.
  8. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 1977, 99, 4599 CrossRef.
  9. F. B. Mallory, K. E. Butler, A. C. Evans, E. J. Brondyke, C. W. Mallory, C. Yang and A. Ellenstein, J. Am. Chem. Soc., 1997, 119, 2119 CrossRef CAS.
  10. M. J. Plater, Tetrahedron Lett., 1995, 35, 6147 CrossRef CAS.
  11. L. Liu, B. Yang, T. Katz and M. Poindexter, J. Org. Chem., 1991, 56, 3769 CrossRef CAS.
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