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

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Abstract

It has been axiomatic for many years that large rings must be prepared under high dilution conditions so that the probability of the two ends meeting exceeds the probability of linear polymer formation7. It therefore seems remarkable that many of the syntheses of macrocyclic polyethers which have been reported involve less than dilute if not very concentrated conditions18. The success of these large-ring intramolecular SN2 reactions is generally attributed to the operation of a “template” effect during crown synthesis.

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References

  1. Chan, L. L., Wong, K. H. and Smid, J.: J. Am. Chem. Soc. (1970) 92, 1955

    Article  CAS  Google Scholar 

  2. Chastrette, M. and Chastrette, F.: J. Chem. Soc. Chem. Commun. (1973) 534

    Google Scholar 

  3. Cook, F. L., Caruso, T. C., Byrne, M. P., Bowers, C. W., Speck, D. H. and Liotta, C. L.: Tetrahedron Letters (1974) 4092

    Google Scholar 

  4. Dale, J. and Daasvatn, K.: J. Chem. Soc. Chem. Commun. (1976) 295

    Google Scholar 

  5. Dale, J. and Kristiansen, P. O.: J. Chem. Soc. Chem. Commun. (1971) 670

    Google Scholar 

  6. Desvergne, J. P. and Bouas-Laurent, H.: J. Chem. Soc. Commun. (1978)403

    Google Scholar 

  7. Eliel, E. L.: Stereochemistry of Carbon Compounds. McGraw Hill, New York 1962, 198 and references therein

    Google Scholar 

  8. Fenton, D. E., Cook, D. H. and Nowell, I. W.: J. Chem. Soc. Chem. Commun. (1977) 274

    Google Scholar 

  9. Gray, R. T., Reinhoudt, D. N., Smit, C. J. and Veenstra, I.: Reel Trav. Chem. Pays-Bas (1976) 95, 258

    Article  CAS  Google Scholar 

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

    Google Scholar 

  11. Izatt, R. M., Terry, R. E., Haymore, B. L., Hansen, L. D., Dalley, N. K., Avondet, A. G. and Christensen, J. J.: J. Am. Chem. Soc. (1976) 98, 7620

    Article  CAS  Google Scholar 

  12. Kawamura, N., Miki, M., Ikeda, I. and Okahara, M.: Tetrahedron Letters (1979) 535

    Google Scholar 

  13. Lehn, J. M., Vierling, P., Hayward, R. G: J. Chem. Soc. Chem. Commun. (1979) 296

    Google Scholar 

  14. Madan, K. and Cram, D. J.: J. Chem. Soc. Chem. Commun. (1975) 427

    Google Scholar 

  15. Mandolini, L. and Masci, B.: J. Am. Chem. Soc. (1977) 99, 7709

    Article  CAS  Google Scholar 

  16. Mandolini, L. and Masci, B.: Synth. Commun. (1979) 9, 851

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. Pedersen, C. J.: J. Am. Chem. Soc. (1967) 89, 7017

    Article  CAS  Google Scholar 

  19. Rastetter, W. H., Phillion, D. P.: Tetrahedron Letters (1979) 1469

    Google Scholar 

  20. Reinhoudt, D. N., de Jong, F. and Tomassen, H. P. M.: Tetrahedron Letters (1979) 2067

    Google Scholar 

  21. Reinhoudt, D. H., Gray, R. T., Smit, C. J. and Veenstra, I.: Tetrahedron (1976) 32, 1161

    Article  CAS  Google Scholar 

  22. Ugelstad, J., Mork, P. C. and Jensen, B.: Acta Chem. Scand. (1963) 27, 1455

    Article  Google Scholar 

  23. Vögtle, F. and Weber, E.: Angew. Chem. Int. Ed. Engl. (1979) 18, 753

    Article  Google Scholar 

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© 1982 Springer-Verlag Berlin Heidelberg

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Gokel, G.W., Korzeniowski, S.H. (1982). The Template Effect. 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_2

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  • DOI: https://doi.org/10.1007/978-3-642-68451-7_2

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68453-1

  • Online ISBN: 978-3-642-68451-7

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