Skip to main content

Syntheses of Azacrowns

  • Chapter
Macrocyclic Polyether Syntheses

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 13))

Abstract

Almost as soon as Pedersen announced his discovery of the crown ethers (see Chaps. 2 and 3) it was recognized by many that these species were similar to those prepared by Busch and coworkers for binding coinage and transition metals (see Sect. 2.1). The latter compounds contained all or a predominance of nitrogen and sulfur (see also Chap. 6) in accordance with their intended use. The crown ethers and the polyazamacrocycles represented two extremes in cation binding ability and preparation of the intermediate compounds quickly ensued. In the conceptual sense, monoazacrowns are the simplest variants of the macrocyclic polyethers and these will be discussed first.

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

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adam, K. R., Lindoy, L. F., Smith, R. J., Anderegg, G., Henrick, K., McPartlin, M. and Tasker, P. A.: J. Chem. Soc., Chem. Commun. (1979) 812

    Google Scholar 

  2. Alcock, N. W. and Tasker, P. A.: J. Chem. Soc., Chem. Commun. (1972) 1239

    Google Scholar 

  3. Ando, N., Yamamoto, Y., Oda, J. and Inouye, Y.: Synthesis (1978) 688

    Google Scholar 

  4. Arnaud-Neu, F., Schwing-Weill, M. J., Louis, R. and Weiss, R.: Inorg. Chem. (1979) 18, 2956

    Article  CAS  Google Scholar 

  5. Atkins, T. J., Richman, J. E. and Oettie, W. F.: Org. Synth. (1978) 58

    Google Scholar 

  6. Beckford, H. F., King, R. M. and Stoddart, J. F., Tetrahedron Letter (1978) 171

    Google Scholar 

  7. Bell, A. P. and Hall, C. D.: J. Chem. Soc., Chem. Commun. (1980) 163

    Google Scholar 

  8. Black, D. St. C. and McLean, I. A.: Chem. Commun. (1968) 1004

    Google Scholar 

  9. Black, D. St. C. and McLean, I. A.: Tetrahedron Letters (1969) 3961

    Google Scholar 

  10. Black, D. St. C. and McLean, I. A.: Aust. J. Chem. (1971) 24, 1401

    Article  CAS  Google Scholar 

  11. Blasius, E., Janzen, K. P. and Newmann, W.: Mikrochimica Acta (1977) II, 279

    Google Scholar 

  12. Bosnich, B., Poon, C. K. and Tobe, M. L.: Inorg. Chem. (1965) 4, 1102

    Article  CAS  Google Scholar 

  13. Boujlel, K. and Simonet, J.: Tetrahedron Letters (1979) 1497

    Google Scholar 

  14. Bovill, M. J., Chadwick, D. J. Johnson, M. R., Jones, N. F., Sutherland, I. O. and Newton, R. F. J. Chem. Soc., Chem. Commun. (1979) 1065

    Google Scholar 

  15. Brown, W. H. and French, W. N: Can. J. Chem. (1958) 36, 371

    Article  CAS  Google Scholar 

  16. Brown, W. H., Hutchinson, B. J. and MacKinnan, M. H.: Can. J. Chem. (1971) 49, 4017

    Article  CAS  Google Scholar 

  17. Buhleier, E., Frensch, K., Luppertz, F. and Vôgtle, F.: Liebigs Ann. Chem. (1978) 1586

    Google Scholar 

  18. Buhleier, E., Rasshofer, W., Wehner, W., Luppertz, F. and Vôgtle, F.: Liebigs Ann. Chem. (1977) 1344

    Google Scholar 

  19. Buhleier, E., Wehner, W. and Vôgtle, F.: Chem. Ber. (1978) 111, 200

    Article  CAS  Google Scholar 

  20. Cinquini, M., Montanari, F. and Tundo, P.: J. Chem. Soc., Chem. Commun. (1975) 393

    Google Scholar 

  21. Cinquini, M. and Tundo, P.: Synthesis (1976) 516

    Google Scholar 

  22. Clay, R. M., Micheloni, M., Paoletti, P. and Steele, W. V.: J. Am. Chem. Soc. (1979) 101, 4120

    Article  Google Scholar 

  23. Cram, D. J.: Ger. Offen. 2,414,188, 21 Nov. 1974

    Google Scholar 

  24. Cresp, T. M. and Sargent, M. V.: J. Chem. Soc. Perkin Trans. I (1973) 1786

    Article  Google Scholar 

  25. Curry, J. D. and Busch, D. H.: J. Am. Chem. Soc. (1964) 86, 592

    Article  CAS  Google Scholar 

  26. DeSarlo, F., Guarno, A. and Speroni, G. P.: J. Chem. Soc., Chem. Commun. (1977) 549

    Google Scholar 

  27. Dietrich, B., Lehn, J. M. and Sauvage, J. P.: Tetrahedron Letters (1969) 2885

    Google Scholar 

  28. Dietrich, B., Fyles, T. M., Lehn, J. M., Pease, L. G. and Fyles, D. L.: J. Chem. Soc., Chem. Commun. (1978) 934

    Google Scholar 

  29. Dishong, D. M., Schultz, R. A. and Gokel, G. W.: unpublished (1980)

    Google Scholar 

  30. Drew, M. G. B., bin Othman, A. H., Mellxoy, P. D. A. and Nelson, S. M.: J. Chem. Soc., Dalton (1975) 2507

    Google Scholar 

  31. Dix, J. P. and Vogtle, F.: Angew. Chem. Int. Ed. Engl. (1978) 17, 857

    Article  Google Scholar 

  32. Dix, J. P. and Vogtle, F.: Angew. Chem. (1978) 90, 893

    Article  CAS  Google Scholar 

  33. Dix, J. P. and Vogtle, F.: Chem. Ber. (1980) 113, 457

    Article  CAS  Google Scholar 

  34. Ehrensperger, C. P., Heberlein, M. and Skrabal, P.: Helv. Chim. Acta (1978) 61, 2813

    Article  CAS  Google Scholar 

  35. Ekstrom, A., Lindoy, L. F. and Smith, R. J.: J. Am. Chem. Soc. (1979) 101, 4014

    Article  CAS  Google Scholar 

  36. Elben, U., Fuchs, H. B., Frenseh, K. and Vogtle, F.: Liebigs Ann. Chem. (1979) 1102

    Google Scholar 

  37. Elben, U. and Vogtle, F.: J. Chem. Res. (S) (1978) 316

    Google Scholar 

  38. Elben, U. and Vogtle, F: J. Chem. Res. (M) (1979) 3791

    Google Scholar 

  39. Fenton, D. E., Cook, D. H., Nowell, I. W. and Walker, P. E.: J. Chem. Soc., Chem. Commun. (1977)623

    Google Scholar 

  40. Girodeau, J. M., Lehn, J. M. and Sauvage, J. P.: Angew. Chem. Int. Ed. Engl. (1975) 14, 764

    Article  Google Scholar 

  41. Gokel, G. W. and Garcia, B. J.: Tetrahedron Letters (1977) 317

    Google Scholar 

  42. Gokel, G. W. and Diamond, C. J.: unpublished (1980)

    Google Scholar 

  43. Gokel, G. W., Timko, J. M. and Cram, D. J.: J. Chem. Soc., Chem. Commun. (1975) 444

    Google Scholar 

  44. Grimsley, P. G., Lindoy, L. F., Lip, H. C., Smith, R. J. and Baker, J. T.: Aust. J. Chem. (1977) 30, 2095

    Article  CAS  Google Scholar 

  45. Greene, R. N.: Tetrahedron Letters (1972) 1793

    Google Scholar 

  46. Hediger, M. and Kaden, T. A.: J. Chem. Soc., Chem. Commun. (1978) 14

    Google Scholar 

  47. Hodgkinson, L. C., Leigh, S. J. and Sutherland, I. O.: J. Chem. Soc., Chem. Commun. (1976) 639

    Google Scholar 

  48. Hodgkinson, L. C. and Sutherland, I. O.: J. Chem. Soc. Perkin. I (1979) 1908

    Google Scholar 

  49. Hodgkinson, L. C., Johnson, M. R., Leigh, S. J., Spencer, N., Sutherland, I. O. and Newton, R. F.: J. Chem. Soc. Perkin. I (1979) 2193

    Google Scholar 

  50. Hogberg, S. A. G. and Cram, D. J.: J. Org. Chem. (1975) 40, 151

    Article  CAS  Google Scholar 

  51. Htay, M. M. and Meth-Cohn, O.: Tetrahedron Letters (1976) 79

    Google Scholar 

  52. Johnson, M. R., Sutherland, I. O. and Newton, R. F.: J. Chem. Soc., Chem. Commun. (1979) 306

    Google Scholar 

  53. Johnson, M. R., Sutherland, I. O. and Newton, R. F.: J. Chem. Soc., Chem. Commun. (1979) 309

    Google Scholar 

  54. Johnson, M. R., Sutherland, I. O. and Newton, R. F.: J. Chem. Soc. Perkin I (1979) 357

    Google Scholar 

  55. Kimura, E., and Yatsunami, T.: Chem. Pharm. Bull. (1980) 28, 994

    CAS  Google Scholar 

  56. Johnson, M. R., Sutherland, I. O. and Newton, R. F.: J. Chem. Soc. Perkin. Trans. I (1980) 586

    Google Scholar 

  57. Kellogg, R. M., Van Bergen, T. J., Van Doren, H., Hedstrand, D., Kool, J., Kruizinga, W. H. and Troostwijk, C. B.: J. Org. Chem. (1980) 45, 2854

    Article  CAS  Google Scholar 

  58. King, A. P. and Krespan, C. G.: J. Org. Chem. (1974) 39, 1315

    Article  CAS  Google Scholar 

  59. Kossai, R., Simonet, J. and Jeminet, G.: Tetrahedron Letters (1979) 1059

    Google Scholar 

  60. Kotzyba-Hibert, F., Lehn, J. M. and Vierling P.: Tetrahedron Letters (1980) 21, 941

    Article  CAS  Google Scholar 

  61. Kramer, U., Guggisberg, A. and Hesse, M.: Helv. Chim. Acta (1979) 62, 2317

    Article  CAS  Google Scholar 

  62. Krespan, C. G.: J. Org. Chem. (1975) 40, 1205

    Article  CAS  Google Scholar 

  63. Krespan, C. G. U.S. Patent 3,952,015, 20 Apr. 1976

    Google Scholar 

  64. Kulstad, S. and Malmsten, L. A.: Acta Chem. Scand., Ser. B (1979) B33, 469

    Article  CAS  Google Scholar 

  65. Kulstad, S. and Malmsten, L. A.: Tetrahedron Letters (1980) 36, 521

    CAS  Google Scholar 

  66. Kulstad, S. and Malmsten, L. A.: Tetrahedron Letters (1980) 21, 643

    Article  CAS  Google Scholar 

  67. Kuo, P. L., Miki, M., Ikeda, I. and Okahara, M.: Tetrahedron Letters (1978) 4273

    Google Scholar 

  68. Kuo, P. L., Miki, M., Ikeda, I. and Okahara, M.: J. Am. Oil Chem. Soc. (1980) 227

    Google Scholar 

  69. Kuwamura, T. and Yoshida, S.: Nippon Kagaku Kaishi (1980) 427

    Google Scholar 

  70. Kyba, E. P., Gokel, G. W., deJong, F., Koga, K., Sousa, L. R., Siegel, M. G., Kaplan, L., Sogah, G. D. Y. and Cram, D. J.: J. Org. Chem. (1977) 42, 4173

    Article  CAS  Google Scholar 

  71. Laidler, D. A. and Stoddart, J. F.: J. Chem. Soc., Chem. Commun. (1976) 979

    Google Scholar 

  72. Lehn, J. M.: U.S. Patent 3,888,877, 10 June 1980

    Google Scholar 

  73. Lehn, J. M. and Vierling, P.: Tetrahedron Letters (1980) 1323

    Google Scholar 

  74. Leigh, S. J. and Sutherland, I. O.: J. Chem. Soc., Chem. Commun. (1975) 414

    Google Scholar 

  75. Leigh, S. J. and Sutherland, I. O.: J. Chem. Soc. Perkin I (1979) 1089

    Google Scholar 

  76. Liang, B. F., Margerum, D. W. and Chung, C. S.: Inorg. Chem. (1979) 18, 2001

    Article  CAS  Google Scholar 

  77. Lockhart, J. C. and Thompson, M. E.: J. Chem. Soc. Perkin Trans. I (1977) 202

    Article  Google Scholar 

  78. Lockhart, J. C., Robson, A. C., Thompson, M. E., Furtado, D., Kaura, C. K. and Allan, A. R.: J. Chem. Soc. Perkin I (1973) 577

    Google Scholar 

  79. Margulis, T. N. and Zompa, L. J.: J. Chem. Soc., Chem. Commun. (1979) 430

    Google Scholar 

  80. Mathias, L. J. Al-Jumah, K.: Organic Coatings and Plastics Chemistry, Vol. 42, ACS (1980) 262

    CAS  Google Scholar 

  81. Metcalfe, J. C., Stoddart, J. F. and Jones, G.: J. Am. Chem. Soc. (1977) 99, 8317

    Article  CAS  Google Scholar 

  82. Mitsubishi Chemical Industries, Japan Kokai 78:91,327, 26 July 1978

    Google Scholar 

  83. Mitsubishi Chemical Industries, Japan Kokai 78:91,328, 9 Feb. 1980

    Google Scholar 

  84. Mitsubishi Chemical Industries, Japan Kokai 78:91,331, 26 July 1978

    Google Scholar 

  85. Okahara, M.: Japan Kokai 78:33,319, 22 Mar. 1978

    Google Scholar 

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

    Article  CAS  Google Scholar 

  87. Newcomb, M., Timko, J. M., Walba, D. M. and Cram, D. J.: J. Am. Chem. Soc. (1977) 99, 6392

    Article  CAS  Google Scholar 

  88. Newkome, G. R. and Hager, D. C.: J. Am. Chem. Soc. (1978) 100, 5567

    Article  CAS  Google Scholar 

  89. Newkome, G. R. and Kawato, T.: J. Org. Chem. (1979) 44, 2693

    Article  CAS  Google Scholar 

  90. Newkome, G. R. and Kawato, T.: J. Am. Chem. Soc. (1979) 101, 7088

    Article  CAS  Google Scholar 

  91. Newkome, G. R. and Kawato, T.: Tetrahedron Letters (1978) 4643

    Google Scholar 

  92. Newkome, G. R., Kawato, T. and Nayak, A.: J. Org. Chem. (1979) 44, 2697

    Article  CAS  Google Scholar 

  93. Newkome, G. R., Kohli, D. K. and Fronczek, F.: J. Chem. Soc., Chem. Commun. (1980) 9

    Google Scholar 

  94. Newkome, G. R., Nayak, A., Fronczek, F., Kawato, T., Taylor, H. C. R., Meade, L. and Mattice, W.: J. Am. Chem. Soc. (1979) 101, 4472

    Article  CAS  Google Scholar 

  95. Newkome, G. R., Nayak, A., Sauer, J. D., Mattschei, P. K., Watkins, S. F., Fronczek, F. and Benton, W. H.: J. Org. Chem. (1979) 44, 3816

    Article  CAS  Google Scholar 

  96. Newkome, G. R., McClure, G. L., Simpson, J. B. and Danesh-Khoshboo, F.: J. Am. Chem. Soc. (1975) 97, 3232

    Article  CAS  Google Scholar 

  97. Newkome, G. R., Nayak, A., McClure, G. L., Danesh-Khoshboo, F. and Broussard-Simpson, J.: J. Org. Chem. (1976) 42, 1500

    Article  Google Scholar 

  98. Newkome, G. R., Nayak, A., Otemaa, J., Van, D. A. and Benton, W. H.: J. Org. Chem. (1978) 43, 3362

    Article  CAS  Google Scholar 

  99. Newkome, G. R. and Robinson, J. M.: J. Chem. Soc., Chem. Commun. (1973) 831

    Google Scholar 

  100. Newkome, G. R., Sauer, J. D., Mattschei, P. K. and Nayak, A.: Heterocycles (1978) 9, 1555

    Article  CAS  Google Scholar 

  101. Pedersen, C. J. and Bromels, M. H.: U.S. Patent 3,847,949,12 Nov. 1974

    Google Scholar 

  102. Pedersen, C. J. and Bromels, M. H.: U.S. Patent 4,031,111, 21 June 1977

    Google Scholar 

  103. Pelissard, D. and Louis, R.: Tetrahedron Letters (1972) 4589

    Google Scholar 

  104. Petranek, J. and Ryba, O.: Tetrahedron Letters (1977) 4249

    Google Scholar 

  105. Richman, J. E.: Tetrahedron Letters (1977) 559

    Google Scholar 

  106. Richman, J. E. and Atkins, T. J.: J. Am. Chem. Soc. (1974) 96, 2268

    Article  CAS  Google Scholar 

  107. Rasshofer, W., Miiller, W. M., Oepen, G. and Vogtle, F.: J. Chem. Research (S) (1978) 72; J. Chem. Research (M) (1978) 1001

    Google Scholar 

  108. Rasshofer, W. and Vogtle, F.: Liebigs Ann. Chem. (1978) 552

    Google Scholar 

  109. Rasshofer, W. and Vogtle, F.: Liebigs Ann. Chem. (1977) 1340

    Google Scholar 

  110. Rasshofer, W., Wehner, W. and Vogtle, F.: Liebigs Ann. Chem. (1976) 916

    Google Scholar 

  111. Sabatini, L. and Fabbrizzi, L.: Inorg. Chem. (1979) 18, 438

    Article  CAS  Google Scholar 

  112. Samuels, G. J. and Espenson, J. H.: Inorg. Chem (1979) 18, 2587

    Article  CAS  Google Scholar 

  113. Shaw, B. L.: J. Am. Chem. Soc. (1975) 97, 3856

    Article  CAS  Google Scholar 

  114. Sieger, H. Vogtle, F.: Liebigs Ann. Chem. (1980) 425

    Google Scholar 

  115. Tabushi, I. and Fujiyoshi, M.: Heterocycles (1977) 7, 851

    Article  CAS  Google Scholar 

  116. Tabushi, I., Kobuke, Y. and Kato, H.: Jpn. Kokai Tokkyo Koho: 79,130,593, 9 Oct. 1979

    Google Scholar 

  117. Tabushi, I., Kuroda, H., Kato, H., Hirai, T. and Okino, H.: Japan Kokai 77: 106,882, 07 Sep. 1977

    Google Scholar 

  118. Tabushi, I., Okino, H. and Kuroda, Y.: Tetrahedron Letters (1976) 4339

    Google Scholar 

  119. Takagi, M., Tazaki, M. and Ueno, K.: Chem. Letters (1978) 1179

    Google Scholar 

  120. Takagi, M., Tazaki, M. and Ueno, K.: Chem. Letters (1978) 1179

    Google Scholar 

  121. Tomoi, M., Abe, O., Ikeda, M., Kihara, K. and Kakiuchi, H.: Tetrahedron Letters (1978) 3031

    Google Scholar 

  122. Vartanyan, S. A., Akopyan, T. R. and Paronikyan, E. G.: Arm. Khim. Zh. (1978) 31, 349

    CAS  Google Scholar 

  123. Vogtle, F., Muller, W. M. and Weber, E.: Chem. Ber. (1980) 113, 1130

    Article  Google Scholar 

  124. Vogtle, F. and Newmann, P.: Tetrahedron Letters (1970) 115

    Google Scholar 

  125. Vogtle, F. and Weber, E.: Angew. Chem. (1974) 86, 126

    Article  Google Scholar 

  126. Von Deuten, K., Knoeehel, A., Kopf, J., Oehler, J. and Rudolph, G.: J. Chem. Res., Synop. (1979) 358

    Google Scholar 

  127. Vögtle, F. and Dix, P.: Liebigs Ann. Chem. (1977) 1698

    Google Scholar 

  128. Vögtle, F. and Elben, U.: Chem. Bei. (1978) 111, 1434

    Google Scholar 

  129. Vögtle, F., Weber, E., Wehner, W., Nätseher, R. and Grütze, J.: Chem. Zeitung (1974) 98, 562

    Google Scholar 

  130. Weber, E.: Angew. Chem. Int Ed. Engl. (1979) 18, 219

    Article  Google Scholar 

  131. Weber, E. and Vögtie, F.: Chem. Ber. (1976) 109, 1803

    Article  CAS  Google Scholar 

  132. Weber, E. and Vögtle, F.: Liebigs Ann. Chem. (1976) 891

    Google Scholar 

  133. Wudl, F. and Gaeta, F.: J. Chem. Soc., Chem. Commun. (1972) 107

    Google Scholar 

  134. Yamashita, T., Nakamura, H., Takagi, M. and Ueno, K.: Bull. Chem. Soc. Ipn. (1980) 53(6), 1550–4

    Article  CAS  Google Scholar 

  135. Zeigerson, E., Ginzburg, G., Schwartz, N., Luv, Z. and Meyerstein, D.: J. Chem. Soc. (1979) 241

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gokel, G.W., Korzeniowski, S.H. (1982). Syntheses of Azacrowns. In: Macrocyclic Polyether Syntheses. Reactivity and Structure Concepts in Organic Chemistry, vol 13. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68451-7_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-68451-7_4

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68453-1

  • Online ISBN: 978-3-642-68451-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics