New podands with terminal chromogenic moieties derived from formazans

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Alan R. Katritzky, Sergei A. Belyakov, Olga V. Denisko, Uko Maran and Naresh S. Dalal


Abstract

Synthesis of several new podands, bearing various terminal chromophoric functions of formazan (9–11), verdazyl (18–20) and verdazylium salt (21–23) types and having a different length of oligooxyethylene bridge between chromophoric units, is developed. Calculated (Alchemy-2000) and found (EPR data) distances between spin centers in bis-radicals 18–20 correlate well. Such spin-labeled species could be good models for the EPR study of host–guest interactions involving ethylene glycol-based podands.


References

  1. F. Vögtle and E. Weber, Angew. Chem., Int. Ed. Engl., 1979, 18, 753 CrossRef.
  2. B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann and E. Weber, J. Am. Chem. Soc., 1979, 101, 2588 CrossRef.
  3. E. Weber and F. Vögtle, in Host Guest Complex Chemistry I, ed. F. Vögtle, Springer-Verlag, New York, 1981, p. 1 Search PubMed; F. Vögtle, H. Sieger and W. M. Müller, ibid., p. 107 Search PubMed.
  4. B. Tümmler, G. Maass, E. Weber, W. Wehner and F. Vögtle, J. Am. Chem. Soc., 1977, 99, 4683 CrossRef CAS.
  5. E. Weber, W. M. Müller and F. Vögtle, Tetrahedron Lett., 1979, 2335 CrossRef CAS.
  6. H. Sakamoto, S. Ito and M. Otomo, Chem. Lett., 1995, 37 CAS.
  7. Y. Nakatsuji, K. Kita, A. Masuyama and T. Kida, Chem. Lett., 1995, 51 CAS.
  8. B. I. Buzykin, G. N. Lipunova, L. P. Sysoyeva and L. I. Rusinova, Formazan Chemistry, Nauka, Moscow, 1992, pp. 231–280(Russ.) Search PubMed.
  9. O. M. Polumbrik, Russ. Chem. Rev. (Engl. Transl.), 1978, 47, 767 Search PubMed.
  10. K. Mukai, T. Yano and K. Ishizu, Tetrahedron Lett., 1981, 22, 4661 CrossRef CAS.
  11. A. R. Katritzky, S. A. Belyakov and H. D. Durst, Tetrahedron Lett., 1994, 35, 6465 CrossRef.
  12. A. W. Nineham, Chem. Rev., 1955, 55, 355 CrossRef CAS.
  13. S. A. Belyakov, J. Org. Chem. USSR (Engl. Transl.), 1992, 28, 1545.
  14. G. Greber, Makromol. Chem., 1955, 17, 154 CrossRef.
  15. A. R. Katritzky and S. A. Belyakov, Synthesis, 1997, 17 CrossRef CAS.
  16. A. R. Katritzky, S. A. Belyakov, H. D. Durst, R. Xu and N. S. Dalal, Can. J. Chem., 1994, 72, 1849 CAS.
  17. N. S. Dalal, R. Xu, A. R. Katritzky, J. Wu and A. Jesorka, Magn. Reson. Chem., 1994, 32, 721 CAS and references therein.
  18. Alchemy-2000, Tripos, Inc., St. Louis, MO, 1996 Search PubMed.
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