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Cryptands and Related Polycyclic Systems

  • Chapter
Macrocyclic Polyether Syntheses

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

Abstract

In 1969, Dietrich, Lehn and Sauvage22 published the first report of a type of molecule which was to engender tremendous interest in the chemical community. These compounds were macrobicyclic polyethers having nitrogen pivot atoms and exhibiting the ability to bind a variety of metal cations. The syntheses of the first examples of macrobicyclic amines were carried out as illustrated in Eq. (8.1). The appropriate diaminopolyether and polyether diacyl chloride were condensed under high dilution conditions to give diamide 1 in 80% yield. Reduction was then effected using LiAlH4 to tetrahydrofuran to yield diamine 2 in 75% yield. A second equivalent of the diacyl chloride used in the first step was allowed to react with 2 (again, high dilution) affording the macrobicyclic diamide 3 in 45% yield. Reduction using diborane afforded the compound called [2.2.2]-cryptand (4) as its bis-borane adduct. Removal of the borane residues could be effected by treatment with 6 N HC1 affording 4 in more than 90% yield from 3. The overall yield for the process was about 25%.

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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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© 1982 Springer-Verlag Berlin Heidelberg

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Gokel, G.W., Korzeniowski, S.H. (1982). Cryptands and Related Polycyclic Systems. 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_8

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  • DOI: https://doi.org/10.1007/978-3-642-68451-7_8

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68453-1

  • Online ISBN: 978-3-642-68451-7

  • eBook Packages: Springer Book Archive

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