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Reactivity of π-equivalent medium-ring nitrogen heterocycles. Azocines and homoazocines

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Chemistry of Heterocyclic Compounds Aims and scope

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Literature cited

  1. The initial synthesis of I was reported by R. Willstätter and E. Waser, Dtsch. Chem. Ges.,44, 3423 (1911); R. Willstätter and M. Heidelberger, ibid.,46, 517 (1913). The current commercial method of production was developed by W. Reppe, O. Schlichting, K. Klager, and T. Toepel, Ann.,560, 1 (1948).

    Google Scholar 

  2. For reviews of this subject, consult: (a) G. Schröder, “Cyclooctatetraen,” Verlag Chemie, GmbH, Weinheim/Bergstr. (1965); (b) L. A. Paquette, Trans. N. Y. Acad. Sci., 357 (1974); (c) L. A. Paquette, Tetrahedron,31, 2855(1975).

  3. G. Schröder, Angew. Chem.,75, 722 (1963); Chem. Ber.,97, 3140 (1964).

    Google Scholar 

  4. G. F. Emerson, L. Watts, and R. Pettit, J. Am. Chem. Soc.,87, 131 (1965); L. Watts, J. D. Fitzpatrick, and R. Pettit, ibid.,87, 3253 (1965).

    Google Scholar 

  5. T. J. Katz and P. J. Garratt, J. Am. Chem. Soc.,85, 2852 (1963); E. A. Lalancette and R. E. Benson, ibid.,85, 2853 (1963).

    Google Scholar 

  6. A. G. Anderson, Jr., W. F. Harrison, and R. G. Anderson, J. Am. Chem. Soc.,85, 3448 (1963).

    Google Scholar 

  7. L. A. Paquette and T. Kakihana, J. Am. Chem. Soc.,90, 3897 (1968); L. A. Paquette, T. Kakihana, J. F. Hansen, and J. C. Philips, ibid.,93, 152 (1971).

    Google Scholar 

  8. D. W. McNeil, M. E. Kent, E. Hedaya, P. F. D'Angelo, and P. O. Schiessel, J. Am. Chem. Soc.,93, 3817 (1971).

    Google Scholar 

  9. 1,2-Diazocine also shares this sensitivity: B. M. Trost and R. M. Cory, J. Am. Chem. Soc.,93, 5573 (1971).

    Google Scholar 

  10. L. A. Paquette, T. Kakihana, J. F. Kelly, and J. R. Malpass, Tetrahedron Lett., 1455 (1968); L. A. Paquette, T. Kakihana, and J. F. Kelly, J. Org. Chem.,36, 435 (1971).

  11. H. L. Strauss, T. J. Katz, and G. K. Fraenkel, J. Am. Chem., Soc.,85, 2360 (1963).

    Google Scholar 

  12. L. C. Snyder, J. Phys. Chem.,66, 2299 (1962); C. A. Coulson, Tetrahedron,12, 193 (1961); N. L. Allinger, J. Org. Chem.,27, 443 (1962).

    Google Scholar 

  13. T. J. Katz, J. Am. Chem. Soc.,82, 3784, 3785 (1960).

    Google Scholar 

  14. L. A. Paquette, J. F. Hansen, and T. Kakihana, J. Am. Chem. Soc.,93, 168 (1971).

    Google Scholar 

  15. L. A. Paquette, T. Kakihana, and J. F. Hansen, Tetrahedron Lett., 529 (1970).

  16. L. A. Paquette and T. Kakihana, J. Am. Chem. Soc.,93, 174 (1971).

    Google Scholar 

  17. L. B. Anderson and L. A. Paquette, J. Am. Chem. Soc.,94, 4915 (1972) and references contained therein.

    Google Scholar 

  18. L. A. Paquette, J. F. Hansen, T. Kakihana, and L. B. Anderson, Tetrahedron Lett., (1970); L. B. Anderson, J. F. Hansen, T. Kakihana, and L. A. Paquette, J. Am. Chem. Soc.,93, 161 (1971).

  19. L. A. Paquette, L. B. Anderson, J. F. Hansen, S. A. Lang, Jr., and H. C. Berk, J. Am. Chem. Soc.,94, 4907 (1972).

    Google Scholar 

  20. S. V. Ley and G. D. Ewing, unpublished work in this laboratory.

  21. L. A. Paquette, H. C. Berk, and S. V. Ley, J. Org. Chem.,40, 902 (1975).

    Google Scholar 

  22. S. V. Ley and L. A. Paquette, J. Am. Chem. Soc.,96, 6670 (1974).

    Google Scholar 

  23. L. A. Paquette, S. V. Ley, S. G. Traynor, J. T. Martin, and J. M. Geckle, J. Am. Chem. Soc.,98, 8162 (1976).

    Google Scholar 

  24. R. Rieke, M. Ogliaruso, R. McClung, and S. Winstein, J. Am. Chem. Soc.,88, 4729 (1966); S. Winstein, G. Moshuk, R. Rieke, and M. Ogliaruso, ibid.,95, 2624 (1973).

    Google Scholar 

  25. T. J. Katz and C. Talcott, J. Am. Chem. Soc.,88, 4732 (1966).

    Google Scholar 

  26. F. J. Smentowski, R. M. Owans, and B. D. Faulion, J. Am. Chem. Soc.,90, 1537 (1968).

    Google Scholar 

  27. G. Moshuk, G. Petrowski, and S. Winstein, J. Am. Chem. Soc.,90, 2179 (1968).

    Google Scholar 

  28. W. H. Okamura, T. I. Ito, and P. M. Kellett, Chem. Commun., 1317 (1971); T. I. Ito, F. C. Baldwin, and W. H. Okamura, ibid., 1440 (1971).

  29. M. Barfield, R. B. Bates, W. A. Beavers, I. R. Blacksburg, S. Brenner, B. I. Mayall, and C. S. McCulloch, J. Am. Chem. Soc.,97, 900 (1975).

    Google Scholar 

  30. E. Vogel and H. Kiefer, Angew. Chem.,73, 548 (1961); E. Vogel, Angew. Chem. Intern. Ed. Engl.,2, 1 (1963).

    Google Scholar 

  31. M. B. Sohn, M. Jones, Jr., and B. Fairless, J. Am. Chem. Soc.,94, 4774 (1972).

    Google Scholar 

  32. A. G. Anastassiou and R. C. Griffith, Chem. Commun., 1301 (1971); 399 (1972); Tetrahedron Lett., 3067 (1973); J. Am. Chem. Soc.,95, 2379 (1973).

  33. J. M. Brown and M. M. Ogilvy, J. Am. Chem. Soc.,96, 292 (1974).

    Google Scholar 

  34. C. P. Lewis and M. Brookhart, J. Am. Chem. Soc.,97, 651 (1975).

    Google Scholar 

  35. L. A. Paquette and T. J. Barton, J. Am. Chem. Soc.,89, 5480 (1967); L. A. Paquette, T. J. Barton, and E. B. Whipple, ibid.,89, 5481 (1967); L. A. Paquette, J. R. Malpass, G. R. Krow, and T. J. Barton, ibid.,91, 5296 (1969).

    Google Scholar 

  36. L. A. Paquette and J. R. Malpass, J. Am. Chem. Soc.,90, 7151 (1968); L. A. Paquette, J. R. Malpass, and G. R. Krow, ibid.,92, 1980 (1970).

    Google Scholar 

  37. H. Klose and H. Günther, Chem. Ber.,102, 2230 (1969).

    Google Scholar 

  38. G. Schröder, J. F. M. Oth, and R. Meranyi, Angew. Chem. Intern. Ed. Engl.,4, 752 (1965).

    Google Scholar 

  39. A. G. Anastassiou and R. C. Griffith, Chem. Commun., 1301 (1971).

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Authors and Affiliations

  1. Evans Chemical Laboratories, Ohio State University, 43210, Columbus, Ohio, USA

    L. A. Paquette

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Translation published in Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–157, February, 1978.

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Paquette, L.A. Reactivity of π-equivalent medium-ring nitrogen heterocycles. Azocines and homoazocines. Chem Heterocycl Compd 14, 111–119 (1978). https://doi.org/10.1007/BF00945319

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  • DOI: https://doi.org/10.1007/BF00945319

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