Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Catalytic and Stoichiometric Synthesis of Ferrocene-Containing Polyazamacrocycles and Chelating Bidentate Nitrogen Ligands

  • Published : 1997.06.20
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Abstract

A series of ferrocene-containing chelating bidentate nitrogen ligands (1 & 2) and polyazamacrocycles (3 & 4) were prepared in high yields from the reaction of ferrocenecarboxaldehydes with corresponding diamines under various catalytic and stoichiometric reaction conditions. The stoichiometric condensation to form Schiff bases required the presence of MgSO₄in the reaction mixture as a water-absorbent. Employment of cyclic diamines such as 1,2-diaminocyclohexane and p-phenylenediamine in the reaction with 1,1'-ferrocenedicarboxaldehyde resulted in the formation of polymers in stead of the expected macrocycles. All these compounds were characterized by microanalytical and spectroscopic techniques. In one case, the structure of 3a was confirmed by X-ray crystallography.

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References

  1. Ferrocene Togni, A.(ed.);Hayashi, T.(ed.)
  2. Asymmetric Catalysis in Organic Synthesis Noyori, R.
  3. Catalytic Asymmetric Synthesis Ojima, I.(Ed.)
  4. Handbook of Enantioselective Catalysis with Transition Metal Compounds v.I Brunner, H.;Zettlmeier, W.
  5. Chem. Rev. v.92 Sawamura, M.;Ito, Y.
  6. J. Am. Chem. Soc. v.118 Sawamura, M.;Sudoh, M.;Ito, Y.
  7. J. Am. Chem. Soc. v.116 Togni, A.;Breutel, C.;Schnyder, A.;Spindler, A.;Landert, H.;Tijani, A.
  8. Ferrocene Hall, C. D.;Togni, A.(ed.);Hayashi, T.(ed.)
  9. Chem. Rev. v.94 van Veggel, F. C. M.;Verboom, W.;Reinhoudt, D.
  10. J. Organomet. Chem. v.441 Beer, P. D.;Nation, J. E.;Harman, M. E.;Hursthouse, M. B.
  11. J. Chem. Soc., Chem. Commun. Beer, P.;Kocian, O.;Mortimer, R. J.;Spencer, P.
  12. J. Chem. Soc., Chem. Commun. Hall, C. D.;Sharpe, N. W.;Danks, I. P.;Sang, Y. P.
  13. J. Organomet. Chem. v.511 Beer, P. D.;Drew, M. G. B.;Hesek, D.;Lacy, S. M.
  14. J. Poly. Sci. v.34 Kim, T. J.;Lee, S. J.;Shim, S. C.
  15. Bull. Korean Chem. Soc. v.16 Kim, T. J.;Kim, D. H.;Shim, S. C.;Jeong, J. H.
  16. J. Organomet. Chem. v.412 Balavoine, G. G. A.;Doisneau, G.;Fillebeen-Khan, T.
  17. J. Organomet. Chem. v.27 Bishop, J. J.;Davison, A.;Katcher, M. L. D.;Lichtenberg, W.;Merril, R. E.;Smart, J. C.
  18. Bull. Korean Chem. Soc. v.10 Kim, T. J.;Lee, K. C.
  19. Inorganic Synthesis v.12 Hallman, P. S.;Stephenson, T. A.;Wilkinson, G.
  20. Purification of Labortory Chemicals(2nd ed.) Perin, D. D.;Armarego, W. L. F.;Perin, D. R.
  21. Inorg. Chem. v.32 Benito, A.;Cano, J.;Martinez-Manez, R.;Soto, J.;Paya, J.;Lioret, F.;Julve, M.;Faus, J.;Marcos, M. D.
  22. Bull. Chem. Soc. Jpn. v.41 Takegami, Y.;Watanabe, Y.;Kanaya, I.;Mitsudo, T.;Okajima, T.;Morishima, Y.;Masada, H.
  23. J. Heterocyclic Chem. v.25 Shim, S. C.;Doh, C. H.;Kim T. J.;Lee, H. K.;Kim, K. D.
  24. J. Chem. Soc., Dalton Trans. Tendro, M. J. L.;Benito, A.;Manez, R. M.;Soto, J.;Paya, J.;Edwards A. J.;Raithby, P. R.
  25. SHELXS-86. Program for the solution of crystal structure determination Sheldrick, G. M.
  26. SHELXS-93. Program for the solution of crystal structure determination Sheldrick, G. M.
  27. J. Chem. Soc., Dalton Trans. Bracci, M.;Ercolani, C.;Floris, B.;Bassetti, M.;Chiesi-Villa, A.;Guastini, C.
  28. New J. Chem. v.16 Chambron, J. C.;Coudret, C.;Sauvage, J. P.
  29. Organometallics v.7 Neuse, E. W.;Meirim, M. G.;Blom, N. F.
  30. J. Mol. Cat. v.62 Shim, S. C.;Doh, C. H.;Woo, B. W.;Kim, H. S.;Huh, K. T.;Park, W. H.;Lee, H.
  31. Bull. Chem. Soc. Jpn. v.60 Tsuji, Y.;Yokoyama, Y.;Huh, K. T.;Watanabe, Y.
  32. J. Org. Chem. v.50 Tsuji, Y.;Huh, T. T.;Ohsugi, Y.;Watanabe, Y.
  33. Chem. Rev. v.90 Brunet, J. J.
  34. Advanced Organic Chemistry(2nd ed.) March, J.
  35. The Chemistry of the Carbon-Nitrogen Double Bond Harada, K.;Patai, S.(Ed.)
  36. Inorg. Chem. v.33 Ball, G. E.;Cullen, W. R.;Fryzuk, M. D.;Henderson, W. J.;James, B. R.;MacFarlane, K. S.
  37. Inorg. Chem. v.30 Becalski, A. G.;Cullen, W. R.;Fryzuk, M. D.;James, B. R.;Kang, G. J.;Rettig, S. J.
  38. J. Mol. Catal. v.62 Cullen, W. R.;Fryzuk, M. D.;James, B. R.;Kutney, J. P.;Kang, G. J.;Herb, G.;Thorburn, I. S.;Spogliarich, R.
  39. Angew. Chem. Int. Ed. Engl. v.29 Spindler, F.;Pugin, B.;Blaster, H.-U.
  40. J. Am. Chem. Soc. v.112 Chan, Y. N. C.;Osborn, J. A.
  41. Polyhedron v.5 Longley, C. J.;Goodwin, T. J.;Wilkinson, G.
  42. J. Mol. Catal. v.22 Vastag, S.;Bakos, J.;Toros, S.;Takach, N. E.;King, R. B.;Heil, B.;Marko, L.
  43. Organometallics v.2 Cullen, W. R.;Kim, T. J.;Einstein, F. W. B.;Jones, T.
  44. Organometallics v.4 Cullen, W. R.;Kim, T. J.;Einstein, F. W. B.;Jones, T.