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Crown Esters and Macrocyclic Polyether Lactones

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Macrocyclic Polyether Syntheses

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

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Abstract

In 1930, in one of many pioneering studies, Carothers showed that certain condensation polymers could be cyclic or macrocyclic rather than exclusively linear21. In addition to this very important observation, he showed that thermolysis in vacuo of certain polymers could also yield macrocyclic materials. Quite a number of papers have been published on this subject since that time, especially dealing with the chemistry of phthalate15,22,24,25,26,27,30, isophthalate5,10,15,44, and terephthalate esters15,32,33,34,49,62,64,77. Many of these structures are tabulated at the end of this chapter.

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References

  1. Akopyan, T. R., Paronikyan, E. G., Sarkisyan, T. P., Avakimyan, D. A.: Arm. Khim. Zh. (1979) 52(9), 716

    Google Scholar 

  2. Ammann, D., Pretsch, E., Simon, W.: Helv. Chim. Acta (1973) 56, 1780

    Article  CAS  Google Scholar 

  3. Asay, R. E., Bradshaw, J. S., Nielsen, S. F., Thompson, M. D., Snow, J. W., Masihdas, D. R. K., Izatt, R. M., Christensen, J. J.: J. Heterocyclic Chem. (1977) 14, 85

    Article  CAS  Google Scholar 

  4. Ashby, J., Hull, R., Cooper, M. J., Ramage, E. M.: Synth. Commun. (1974) 113

    Google Scholar 

  5. Berr, C. E.: J. Polymer Science (1955) 15, 591

    Article  CAS  Google Scholar 

  6. Bobranski, B., Sladowska, H.: Rocz. Chem. Ann. Soc. Chem. Polon. (1972) 46, 459

    CAS  Google Scholar 

  7. Bogatsky, A. V., Lukyanenko, N. G., Kirichenko, T. I.: Tetrahedron Letters (1980) 313

    Google Scholar 

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

    Article  CAS  Google Scholar 

  9. Bradshaw, J. S., Asay, R. E., Baxter, S. L., Fore, P. E., Jolley, S. T., Lamb, J. D., Maas, G. E., Thompson, M. D., Izatt, R. M., Christensen, J. J.: Ind. Eng. Chem. Prod. Res. Dev. (1980) 19, 86

    Article  CAS  Google Scholar 

  10. Bradshaw, J. S., Baxter, S. L., Scott, D. C., Lamb, J. D., Izatt, R. M., Christensen, J. J.: Tetrahedron Letters (1979) 3383

    Google Scholar 

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

    Article  Google Scholar 

  12. Bradshaw, J. S., Hansen, L. D.; Nielsen, S. F., Thompson, M. D., Reeder, R. A., Izatt, R. M., Christensen, J. J.: J. C. S. Chem. Comm. (1975) 874

    Google Scholar 

  13. Bradshaw, J. S., Maas, G. E., Izatt, R. M., Lamb, J. D., Christensen, J. J.: Tetrahedron Letters (1979)635

    Google Scholar 

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

    Article  CAS  Google Scholar 

  15. Bradshaw, J. S., Thompson, M. D.: J. Org. Chem. (1978) 45, 2456

    Article  Google Scholar 

  16. British Pat. 942,865, 27 Nov. 1963

    Google Scholar 

  17. British Pat. 1,047,767a, 9 Nov. 1966

    Google Scholar 

  18. Buhleier, E., Frensch, K., Luppertz, F., Vögtle, F.: Liebigs Ann. Chem. (1978) 1586

    Google Scholar 

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

    Article  CAS  Google Scholar 

  20. Buhleier, E., Wehner, W., Vögtle, F.: Liebigs Ann. Chem. (1978) 537

    Google Scholar 

  21. Carothers, W. H., Dorough, G. L.: J. Am. Chem. Soc. (1930) 52, 711

    Article  CAS  Google Scholar 

  22. Crawford, L, M. R., Drewes, S. E., Sutton, D. A.: Chem. & Ind. (1970) 1351

    Google Scholar 

  23. DeVries, J. G-, Kellogg, R. M.: J. Am. Chem. Soc. (1979) 101, 2759

    Article  CAS  Google Scholar 

  24. Drewes, S. E., Coleman, P. C.: I. C. S. Perkin Trans. I (1972) 2148

    Article  Google Scholar 

  25. Drewes, S. E., Coleman, P. C.: J. C. S. Perkin Trans. I (1974) 2578

    Article  Google Scholar 

  26. Drewes, S. E., Riphagen, B. G.: J. C. S. Perkin Trans. I (1974) 323

    Article  Google Scholar 

  27. Drewes, S. E., Riphagen, B. G.: J. C. S. Perkin Trans. I (1974) 1908

    Article  Google Scholar 

  28. Drewes, S. E., Riphagen, B. G.: J. C. S. Perkin Trans. I (1976) 2574

    Article  Google Scholar 

  29. Ehrhart, W. A. J. Org. Chem. (1968) 43, 2930

    Article  Google Scholar 

  30. Ehrhart, W. A.: U.S. Patent 3,431,279 4 Mar. 1969

    Google Scholar 

  31. Fore, P. E., Bradshaw, J. S., Nielsen, S. F.: J. Heterocycl. Chem. (1978) 15, 269

    Article  CAS  Google Scholar 

  32. Frensch, K., Vogtle, F.: Tetrahedron Letters (1977) 2573

    Google Scholar 

  33. Frensch, K-, Vogtle, F.: J. Org. Chem. (1979) 44, 884

    Article  CAS  Google Scholar 

  34. Goodman, I., Nesbitt, B. F.: Brit Patent 851,369,12 Oct. 1960

    Google Scholar 

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

    Google Scholar 

  36. Izatt, R. M., Lamb, J. D., Asay, R. E., Mass, G. E., Bradshaw, J. S., Christensen, J. J.: J. Am. Chem. Soc. (1977) 99, 6134

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  38. Jolly, S. T., Bradshaw, J. S.: J. Org. Chem. (1980) 45, 3554

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  40. Knutov, V. I., Butin, M. K., Voronkov, M. G.: Khim. Geterotsikl. Soedin. (1980) 123

    Google Scholar 

  41. Koegel, W., Schroeder, G.: Tetrahedron Letters (1978) 623

    Google Scholar 

  42. Kudrya, T. N., Shtepanek, A. S., Kirsanov A. V.: Zh. Obshch. Khim. (1978) 48, 844

    Google Scholar 

  43. Kudrya, T. N., Shtepanek, A. S., Kirsanov, A. V.: Zh. Obshch. Khim. (1978) 48, 927

    CAS  Google Scholar 

  44. Kudrya, T. N., Talanova, G. G., Bonadyk, S. V., Sinitsa, A. D.: Dopov. Akad. Nauk., UKr. RSR. Geol., Khim. Biol. Nauki (1979) 6, 434 [Chem. Abstr. (1980) 91, 175313k]

    Google Scholar 

  45. Lamb, J. D., Izatt, R. M., Swain, C. S., Bradshaw, J. S., Christensen, J. J.: J. Am. Chem. Soc. (1980) 102, 479

    Article  CAS  Google Scholar 

  46. Lesiak, J., Boucher, M. N., Descotes, G.: Synthesis (1980) 240

    Google Scholar 

  47. Liptuga, N. I., Irodionova, L. F., Lozinskii, M. O.: Zh. Obshch. Khim. (1978) 48, 1085

    Google Scholar 

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

    Article  CAS  Google Scholar 

  49. Matsushima, K., Kawamura, N., Okahara, M.: Tetrahedron Letters (1979) 3445

    Google Scholar 

  50. Meraskentis, E., Zahn, H., Chem. Ber. (1970) 103, 3034

    Article  CAS  Google Scholar 

  51. Mirabella, F. M., Sheean, D. H.: Ger. Offen. 1,929,550, 2 Jan. 1970

    Google Scholar 

  52. Moody, L. S.: U.S. Patent 3,155,683, 3 Nov. 1964

    Google Scholar 

  53. Newkome, G. R., Kawato, T., Benton, W. H.: J. Org. Chem. (1980) 45, 626

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  56. Ors, J. A., Srinivasan, R.: J. Am. Chem. Soc. (1978) 100, 315

    Article  CAS  Google Scholar 

  57. Ors, J. A., Srinivasan, R.: J. C. S. Chem. Commun. (1978) 400

    Google Scholar 

  58. Pedersen, C. J.: J. Am. Chem. Soc. (1970) 92, 391

    Article  CAS  Google Scholar 

  59. Pedersen, C. J.: J. Org. Chem. (1971) 36, 254

    Article  CAS  Google Scholar 

  60. Pedersen, C. J.: U.S. Patent 3,987,061, 19 Oct. 1976

    Google Scholar 

  61. Piepers, O., Kellogg, R. M.: J.C.S. Chem. Commun. (1978) 383

    Google Scholar 

  62. Prochaska, R. J.: U.S. Patent 3,274,214, 20 Sept. 1966

    Google Scholar 

  63. Repin, H., Papanikolan, E.: J. Polymer Sci. (1967) 7, A-l, 3426

    Google Scholar 

  64. Sakamoto, K., Oki, M.: Chem. Lett. (1975) 615

    Google Scholar 

  65. Sakamoto, K., Oki, M.: Bull. Chem. Soc. Japan (1976) 49, 3159

    Article  CAS  Google Scholar 

  66. Samat, A., Elguero, J., Metzger, J.: J. C. S. Chem. Commun. (1979) 1182

    Google Scholar 

  67. Shanzer, A., Mayer-Shochet, N.: J. C. S., Chem. Commun. (1980) 176

    Google Scholar 

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

    Google Scholar 

  69. Stueben, K. C.: J. Polymer Sci. (1966) 4, A-l, 829

    CAS  Google Scholar 

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

    Google Scholar 

  71. Van Bergen, T. J., Kellogg, R. M.: J. C. S. Chem. Commun. (1976) 964;

    Google Scholar 

  72.  Van der Veen, R. H., Kellogg, R. M., Vos, A., Van Bergen, T. J., J. C. S. Chem. Commun. (1978), 923

    Google Scholar 

  73. Van Keulen, B. J., Kellogg, R. M., Piepers, O.: J. C. S. Chem. Commun. (1979) 285

    Google Scholar 

  74. Vögtle, F., Newmann, P.: Tetrahedron Letters (1970) 115

    Google Scholar 

  75. Vögtle, F., Weber, E., Wehner, W., Nätscher, R., Grütze, J.: Chem. Zeitung (1974) 98, 562

    Google Scholar 

  76. Vorländer, D.: Liebigs Ann. Chem. (1894) 280, 167

    Article  Google Scholar 

  77. Weber, E., Vögtle, F.: Chem. Ber. (1976) 109, 1803

    Article  CAS  Google Scholar 

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

    Google Scholar 

  79. Zahn, H., Repin, J. F.: Chem. Ber. (1970) 103, 3041

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Maryland, 20742, College Park, MD, USA

    Professor George W. Gokel

  2. Chemicals and Pigments Department, Jacson Laboratory, E. I. Du Pont de Nemours Co., Inc., 08023, Deepwater, New Jersey, USA

    Dr. Stephen H. Korzeniowski

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  1. Professor George W. Gokel
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  2. Dr. Stephen H. Korzeniowski
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Gokel, G.W., Korzeniowski, S.H. (1982). Crown Esters and Macrocyclic Polyether Lactones. 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_5

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  • DOI: https://doi.org/10.1007/978-3-642-68451-7_5

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