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DOI: 10.1039/A700857K (Paper) Reference Section for: Chem. Commun., 1997, 993-994

Tandem 1,3-dipolar cycloadditions of münchnones. Syntheses and molecular structures of 10-azatetracyclo[6.3.0.04,11.05,9]undecanes and azahomopentaprismane

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Gordon W. Gribble, William R. Sponholtz III, Frank L. Switzer, Ferdinando J. D’Amato and Marianne P. Byrn

Abstract

Photocyclization of 10-benzyl-9,11-diphenyl-10-azatetracyclo[6.3.0.04,11.05,9 ]undeca-2,6-diene 11, prepared in one step from münchnone 7 and cycloocta-1,3,5,7-tetraene 10, gives azahomopentaprismane 12.

References

  1. A. P. Marchand, Chem. Rev., 1989, 89, 1011 CrossRef CAS; T.-C. Chou, Y.-L. Yeh and G.-H. Lin, Tetrahedron Lett., 1996, 37, 8779 CrossRef CAS; T. D. Golobish and W. P. Dailey, Tetrahedron Lett., 1996, 37, 3239 CrossRef CAS.
  2. S. L. Sacks, J. R. Scheffer, C.-Z. Teh and A. Tse, J. Med. Chem., 1985, 28, 819 CrossRef CAS; D. P. Becker, R. Nosal, D. L. Zabrowski and D. L. Flynn, Tetrahedron, 1997, 53, 1 CrossRef CAS.
  3. G. W. Gribble and B. H. Hirth, J. Heterocycl. Chem., 1996, 33, 719 CAS; G. W. Gribble, F. Switzer, J. H. Bushweller, J. G. Jewett, J. H. Brown, J. L. Dion, C. H. Bushweller, M. P. Byrn and C. E. Strouse, J. Org. Chem., 1996, 61, 4319 CrossRef CAS; C. H. Bushweller, J. H. Brown, C. M. DiMeglio, G. W. Gribble, J. T. Eaton, C. S. LeHoullier and E. R. Olson, J. Org. Chem., 1995, 60, 268 CrossRef CAS; G. W. Gribble, N. R. Easton, Jr. and J. T. Eaton, Tetrahedron Lett., 1970, 1075 CrossRef CAS.
  4. For the synthesis of pentaprismane, see P. E. Eaton, Y. S. Or and S. J. Branca, J. Am. Chem. Soc., 1981, 103, 2134 Search PubMed; P. E. Eaton, Y. S. Or, S. J. Branca and B. K. R. Shankar, Tetrahedron, 1986, 42, 1621 CrossRef CAS; W. G. Dauben and A. F. Cunningham, Jr., J. Org. Chem., 1983, 48, 2842 CrossRef CAS.
  5. P. M. Weintraub, J. Chem. Soc., Chem. Commun., 1970, 760 RSC.
  6. For a recent study of this reaction, see G. W. Gribble and B. H. Hirth, J. Heterocycl. Chem., 1996, 33, 719 Search PubMed.
  7. R. R. Fraser, G. Boussard, I. D. Postescu, J. J. Whiting and Y. Y. Wigfield, Can. J. Chem., 1973, 51, 1109 CAS.
  8. R. Huisgen, H. Gotthardt, H. O. Bayer and F. C. Schaefer, Chem. Ber., 1970, 103, 2611 CAS.
  9. W. K. Anderson and A. R. Heider, Synth. Commun., 1986, 16, 357 CAS.
  10. G. W. Gribble, F. L. Switzer, J. H. Bushweller, J. G. Jewett, J. H. Brown, J. L. Dion, C. H. Bushweller, M. P. Byrn and C. E. Strouse, J. Org. Chem., 1996, 61, 4319 CrossRef CAS.
  11. K. Saito, Y. Omura, E. Maekawa and P. G. Gassman, Bull. Chem. Soc. Jpn., 1990, 63, 395 CAS.
  12. A. P. Marchand, T.-C. Chou, J. D. Ekstrand and D. van der Helm, J. Org. Chem., 1976, 41, 1438 CrossRef CAS.
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