Skip to main content
Log in

Twenty-five Years of "Crowning" Around: Synthesis of Crown Ethers at Brigham Young University

  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

A review of the synthesis of crown ethers at Brigham Young University ispresented. Topics include: thiacrown ethers, diestercrown ethers,proton-ionizable crown ethers, chiral crown ethers, azacrown ethers,cryptands and other polycyclic ligands, and the Mannich reaction method toprepare azacrown ethers and cryptands.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. C.J. Pedersen: J. Am. Chem. Soc. 89, 7017–7036 (1967).

    Google Scholar 

  2. R.M. Izatt, J.H. Rytting, D.P. Nelson, B.L. Haymore and J.J. Christensen: Science 164, 443–444 (1969).

    Google Scholar 

  3. J.J. Christensen, J.O. Hill and R.M. Izatt: Science 174, 459–467 (1971).

    Google Scholar 

  4. R.M. Izatt, J.S. Bradshaw, S.A. Nielsen, J.D. Lamb, J.J. Christensen and D. Sen: Chem. Rev. 85, 271–339 (1985).

    Google Scholar 

  5. R.M. Izatt, K. Pawlak, J.S. Bradshaw and R.L. Bruening: Chem. Rev. 91, 1721–2085 (1991).

    Google Scholar 

  6. R.M. Izatt, K. Pawlak, J.S. Bradshaw and R.L. Bruening: Chem. Rev. 95, 2529–2586 (1995).

    Google Scholar 

  7. J.S. Bradshaw and R.M. Izatt: Accounts, in press.

  8. R.M. Izatt: J. Incl. Phenom., in press.

  9. J.S. Bradshaw, J.Y. Hui, B.L. Haymore, J.J. Christensen and R.M. Izatt: J. Hetercyclic Chem. 10, 1–4 (1973).

    Google Scholar 

  10. J.S. Bradshaw, J.Y. Hui, Y. Chan, B.L. Haymore, J.J. Christensen and R.M. Izatt: J. Heterocyclic Chem. 11, 45–49 (1974).

    Google Scholar 

  11. J.S. Bradshaw, R.A. Reeder, M.D. Thompson, E.D. Flanders, R.L. Carruth, R.M. Izatt and J.J. Christensen: J. Org. Chem. 41, 134–136 (1976).

    Google Scholar 

  12. J.S. Bradshaw, L.D. Hansen, S.F. Nielsen, M.D. Thompson, R.A. Reeder, R.M. Izatt and J.J. Christensen: J. Chem. Soc., Chem. Commun. 874–875 (1975).

  13. J.S. Bradshaw, C.T. Bishop, S.F. Nielsen, R.E. Asay, D.R.K. Masihdas, E.D. Flanders, L.D. Hansen, R.M. Izatt and J.J. Christensen: J. Chem. Soc., Perkin Trans. 1, 2505–2508 (1976).

    Google Scholar 

  14. M.D. Thompson, J.S. Bradshaw, S.F. Nielsen, C.T. Bishop, F.T. Cox, P.E. Fore, G.E. Maas, R.M. Izatt and J.J. Christensen: Tetrahedron 33, 3317–3320 (1977).

    Google Scholar 

  15. R.M. Izatt, J.D. Lamb, G.E. Maas, R.E. Asay, J.S. Bradshaw and J.J. Christensen: J. Am. Chem. Soc. 99, 2365–2366 (1977).

    Google Scholar 

  16. G.E. Maas, J.S. Bradshaw, R.M. Izatt and J.J. Christensen: J. Org. Chem. 42, 3937–3941 (1977).

    Google Scholar 

  17. M. Newcomb, G.W. Gokel and D.J. Cram: J. Am. Chem. Soc. 96, 6810–6811 (1974).

    Google Scholar 

  18. R.M. Izatt, J.D. Lamb, R.E. Asay, G.E. Maas, J.S. Bradshaw, J.J. Christensen and S.S. Moore: J. Am. Chem. Soc. 99, 6134–6136 (1977).

    Google Scholar 

  19. J.S. Bradshaw, G.E. Maas, J.D. Lamb, R.M. Izatt and J.J. Christensen: J. Am. Chem. Soc. 102, 467–474 (1980).

    Google Scholar 

  20. J.S. Bradshaw, R.E. Asay, G.E. Maas, R.M. Izatt and J.J. Christensen: J. Heterocyclic Chem. 15, 825–831 (1978).

    Google Scholar 

  21. P.E. Fore, J.S. Bradshaw and S.F. Nielsen: J. Heterocyclic Chem. 15, 269–272 (1978).

    Google Scholar 

  22. J.S. Bradshaw and S.T. Jolley: J. Heterocyclic Chem. 16, 1157–1161 (1979).

    Google Scholar 

  23. S.T. Jolley and J.S. Bradshaw: J. Org. Chem. 45, 3554–3559 (1980).

    Google Scholar 

  24. J.S. Bradshaw and M.D. Thompson: J. Org. Chem. 43, 2456–2460 (1978).

    Google Scholar 

  25. K. Frensch and F. Vögtle: J. Org. Chem. 44, 884–885 (1979).

    Google Scholar 

  26. J.S. Bradshaw, S.L. Baxter, J.D. Lamb, R.M. Izatt and J.J. Christensen: J. Am. Chem. Soc. 103, 1821–1827 (1981).

    Google Scholar 

  27. R.B. Davidson, N.K. Dalley, R.M. Izatt, J.S. Bradshaw and C.F. Campana: Israel J. Chem. 25, 33–38 (1985).

    Google Scholar 

  28. J.S. Bradshaw, B.A. Jones, R.B. Nielsen, N.O. Speneer and P.K. Thompson: J. Heterocyclic Chem. 20, 957–962 (1983).

    Google Scholar 

  29. B.A. Jones, J.S. Bradshaw, P.R. Brown, J.J. Christensen and R.M. Izatt: J. Org. Chem. 48, 2635–2639 (1983).

    Google Scholar 

  30. J.S. Bradshaw, M.L. Colter, Y. Nakatsuji, N.O. Spencer, M.F. Brown, R.M. Izatt, G. Arena, P.-K. Tse, B.E. Wilson, J.D. Lamb, N.K. Dalley, F.G. Morin and D.M. Grant: J. Org. Chem. 50, 4865–4872 (1985).

    Google Scholar 

  31. Y. Nakatsuji, J.S. Bradshaw, P.-K. Tse, G. Arena, B.E. Wilson, N.K. Dalley and R.M. Izatt: J. Chem. Soc., Chem. Commun. 749–751 (1985).

  32. J.S. Bradshaw, Y. Nakatsuji, P. Huszthy, B.E. Wilson, N.K. Dalley and R.M. Izatt: J. Heterocyclic Chem. 23, 353–360 (1986).

    Google Scholar 

  33. J.S. Bradshaw, D.A. Chamberlin, P.E. Harrison, B.E. Wilson, G. Arena, N.K. Dalley, J.D. Lamb, R.M. Izatt, F.G. Morin and D.M. Grant: J. Org. Chem. 50, 3065–3069 (1985).

    Google Scholar 

  34. J.S. Bradshaw, R.B. Nielson, P.-K. Tse, G. Arena, B.E. Wilson, N.K. Dalley, J.D. Lamb, J.J. Christensen and R.M. Izatt: J. Heterocyclic Chem. 23, 361–368 (1986).

    Google Scholar 

  35. J.S. Bradshaw, P. Huszthy and R.M. Izatt: J. Heterocyclic Chem. 23, 1673–1676 (1986).

    Google Scholar 

  36. J.F. Biernat, J.S. Bradshaw, B.E. Wilson, N.K. Dalley and R.M. Izatt: J. Heterocyclic Chem. 23, 1667–1671 (1986).

    Google Scholar 

  37. J.F. Biernat, M. Bochenska, J.S. Bradshaw, H. Koyama, G.C. LindH, J.D. Lamb, J.J. Christensen and R.M. Izatt: J. Incl. Phenom. 5, 729–738 (1987).

    Google Scholar 

  38. R.M. Izatt, G.C. LindH, R.L. Bruening, J.S. Bradshaw, J.D. Lamb and J.J. Christensen: Pure Appl. Chem. 58, 1453–1460 (1986).

    Google Scholar 

  39. J.S. Bradshaw, R.M. Izatt, P. Huszthy, Y. Nakatsuji, J.F. Biernat, H. Koyama, C.W. McDaniel, S.G. Wood, R.B. Nielsen, G.C. LindH, R.L. Bruening, J.D. Lamb and J.J. Christensen: Studies in Organic Chemistry 31, 553, H. Kobayashi, Ed., Elsevier Science Publishers, Amsterdam, The Netherlands (1986).

    Google Scholar 

  40. J.S. Bradshaw, J.M. Guynn, S.G. Wood., B.E. Wilson, N.K. Dalley and R.M. Izatt: J. Heterocyclic Chem. 24, 415–419 (1987).

    Google Scholar 

  41. J.S. Bradshaw, J.M. Guynn, S.G. Wood, K.E. Krakowiak, R.M. Izatt, C.W. McDaniel, B.E. Wilson, N.K. Dalley and G.C. LindH: J. Org. Chem. 53, 2811–2816 (1988).

    Google Scholar 

  42. J.T. Redd, J.S. Bradshaw, P. Huszthy and R.M. Izatt: J. Heterocyclic Chem. 31, 1047–1052 (1994).

    Google Scholar 

  43. J.T. Redd, J.S. Bradshaw, P. Huszthy and R.M. Izatt: unpublished observations.

  44. B.A. Jones, J.S. Bradshaw and R.M. Izatt: J. Heterocyclic Chem. 19, 551–556 (1982).

    Google Scholar 

  45. J.S. Bradshaw, P.K. Thompson, R.M. Izatt, E.G. Morin and D.M. Grant: J. Heterocyclic Chem. 21, 897–901 (1984).

    Google Scholar 

  46. S.T. Jolley, J.S. Bradshaw and R.M. Izatt: J. Heterocyclic Chem. 19, 3–19 (1982).

    Google Scholar 

  47. J.S. Bradshaw, P. Huszthy, C.W. McDaniel, C.-Y. Zhu, N.K. Dalley, R.M. Izatt and S. Lifson: J. Org. Chem. 55, 3129–3137 (1990).

    Google Scholar 

  48. P. Huszthy, J.S. Bradshaw, C.-Y. Zhu, R.M. Izatt and S. Lifson: J. Org. Chem. 56, 3330–3336 (1991).

    Google Scholar 

  49. P. Huszthy, M. Oue, J.S. Bradshaw, C.-Y. Zhu, T.-M. Wang, N.K. Dalley, J.C. Curtis and R.M. Izatt: J. Org. Chem. 57, 5383–5394 (1992).

    Google Scholar 

  50. T.M. Wang, J.S. Bradshaw and R.M. Izatt: Gazz. Chim. Ital. 126, 159–164 (1996).

    Google Scholar 

  51. R.M. Izatt, C.-Y. Zhu, N.K. Dalley, J.C. Curtis, X.L. Kou and J.S. Bradshaw: J. Phys. Org. Chem. 5, 656–662 (1992).

    Google Scholar 

  52. R.M. Izatt, T.-M. Wang, P. Huszthy, J.K. Hathaway, X.-X. Zhang, J.C. Curtis, J.S. Bradshaw and C.-Y. Zhu: J. Incl. Phenom. 17, 157–175 (1994).

    Google Scholar 

  53. X.X. Zhang, R.M. Izatt, J.S. Bradshaw and P. Huszthy: Anal. Quim. 92, 64–69 (1996).

    Google Scholar 

  54. X.X. Zhang, R.M. Izatt, P. Huszthy and J.S. Bradshaw,: Chem. Rev. submitted.

  55. Y. Habata, J.S. Bradshaw, J.J. Young, S.L. Castle, P. Huszthy, T. Pyo, M.L. Lee and R.M. Izatt: J. Org. Chem. 61, 8391–8396 (1996).

    Google Scholar 

  56. P.C. Hellier, J.S. Bradshaw, X.X. Zhang, J.J. Young and R.M. Izatt: J. Org. Chem. 61, 7270–7275 (1996).

    Google Scholar 

  57. J.S. Bradshaw, K.E. Krakowiak, R.L. Bruening, B.J. Tarbet, P.B. Savage and R.M. Izatt: J. Org. Chem. 53, 3190–3195 (1988).

    Google Scholar 

  58. J.S. Bradshaw, R.L. Bruening, K.E. Krakowiak, B.J. Tarbet, M.L. Bruening, R.M. Izatt and J.J. Christensen: J. Chem. Soc., Chem. Commun. 812–814 (1988).

  59. K.E. Krakowiak, J.S. Bradshaw, R.M. Izatt and D.J. Zamecka-Krakowiak: J. Org. Chem. 54, 4061–4067 (1989).

    Google Scholar 

  60. J.S. Bradshaw, K.E. Krakowiak and R.M. Izatt: J. Heterocyclic Chem. 26, 1431–1435 (1990).

    Google Scholar 

  61. J.S. Bradshaw, K.E. Krakowiak, R.M. Izatt and D.J. Zamecka-Krakowiak: Tetrahedron Lett. 31, 1077–1080 (1990).

    Google Scholar 

  62. K.E. Krakowiak, J.S. Bradshaw and R.M. Izatt: J. Org. Chem. 55, 3364–3368 (1990).

    Google Scholar 

  63. K.E. Krakowiak, J.S. Bradshaw, W. Jiang, N.K. Dalley, G. Wu and R.M. Izatt: J. Org. Chem. 56, 2675–2680 (1991).

    Google Scholar 

  64. K.E. Krakowiak, J.S. Bradshaw and R.M. Izatt: SynLett. 611–620 (1993).

  65. K.E. Krakowiak, J.S. Bradshaw and D.J. Zamecka-Krakowiak: Chem. Rev. 89, 929–972 (1989).

    Google Scholar 

  66. J.S. Bradshaw, K.E. Krakowiak and R.M. Izatt: Aza-crown macrocycles, John Wiley & Sons, Inc., New York, 1993.

    Google Scholar 

  67. S. Külstad and L.A. Malmsten: Tetrahedron Lett. 21, 643–646 (1980).

    Google Scholar 

  68. K.E. Krakowiak, P.A. Krakowiak and J.S. Bradshaw: Tetrahedron Lett. 34, 777–778 (1993).

    Google Scholar 

  69. K.E. Krakowiak, J.S. Bradshaw, C.-Y. Zhu, J.K. Hathaway, N.K. Dalley and R.M. Izatt: J. Org. Chem. 59, 4082–4086 (1994).

    Google Scholar 

  70. J.S. Bradshaw, H.-Y. An, K.E. Krakowiak, T.-M. Wang, C.-Y. Zhu and R.M. Izatt: J. Org. Chem. 57, 6112–6118 (1992).

    Google Scholar 

  71. J.S. Bradshaw, H.-Y. An, K.E. Krakowiak, G. Wu and R.M. Izatt: Tetrahcdron 46, 6985–6994 (1990).

    Google Scholar 

  72. H.-Y. An, J.S. Bradshaw, K.E. Krakowiak, C.-Y. Zhu, N.K. Dalley and R.M. Izatt: J. Org. Chem. 57, 4998–5005 (1992).

    Google Scholar 

  73. H.-Y. An, J.S. Bradshaw and R.M. Izatt: Chem. Rev. 92, 543–572 (1992).

    Google Scholar 

  74. H.-Y. An, J.S. Bradshaw, K.E. Krakowiak, B.J. Tarbet, N.K. Dalley, K.-L. Kou, C.-Y. Zhu and R.M. Izatt: J. Org. Chem. 58, 7694–7699 (1993).

    Google Scholar 

  75. K.E. Krakowiak and J.S. Bradshaw: J. Heterocyclic Chem. 33, 1–3 (1996).

    Google Scholar 

  76. N.G. Lukyanenko, V.N. Pastushok and A.V. Bordunov: Synthesis 241–242 (1991).

  77. N.G. Lukyanenko, V.N. Pastushok, A.V. Bordunov, V.L. Vetrogon, N.L. Vetrogon and J.S. Bradshaw: J. Chem. Soc., Perkin Trans. 1 1489–1493 (1994).

    Google Scholar 

  78. A.V. Bordunov, N.G. Lukyanenko, V.N. Pastushok, K.E. Krakowiak, J.S. Bradshaw, N.K. Dalley and R.M. Izatt: J. Org. Chem. 60, 4912–4918 (1995).

    Google Scholar 

  79. A.V. Bordunov, N.K. Dalley, X. Kou, J.S. Bradshaw and V.N. Pastushok: J. Heterocyclic Chem. 33, 933–942 (1996).

    Google Scholar 

  80. A.V. Bordunov, P.C. Hellier, J.S. Bradshaw, N.K. Dalley, X. Kou, X.X. Zhang and R.M. Izatt: J. Org. Chem. 60, 6097–6102 (1995).

    Google Scholar 

  81. E.B. Sandell: Photometric Determination of Traces of Metals, 4th ed., John Wiley & Sons, New York, p 415 (1978).

    Google Scholar 

  82. A.V. Bordunov, J.S. Bradshaw, X.X. Zhang, N.K. Dalley, X. Kou and R.M. Izatt: Inorg. Chem. 35, 7229–7240 (1996).

    Google Scholar 

  83. X.X. Zhang, A.V. Bordunov, J.S. Bradshaw, N.K. Dalley, X. Kou and R.M. Izatt: J. Am. Chem. Soc. 117, 11507–11511 (1995).

    Google Scholar 

  84. V.N. Pastushok, J.S. Bradshaw, A.V. Bordunov and R.M. Izatt: J. Org. Chem. 61, 6888–6892 (1996).

    Google Scholar 

  85. V.N. Pastushok, K.-J. Hu, J.S. Bradshaw, N.K. Dalley, A.V. Bordunov and N.G. Lukyanenko: J. Org. Chem., 62, 212–215 (1997).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bradshaw, J.S. Twenty-five Years of "Crowning" Around: Synthesis of Crown Ethers at Brigham Young University. Journal of Inclusion Phenomena 29, 221–246 (1997). https://doi.org/10.1023/A:1007955428644

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1007955428644

Navigation