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Head-to-tail connected double calix[4]arenes

Doppelte Calix[4]arene in Kopf-Schwanz-Verknüpfung

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

New macrotricyclic compounds consisting of two calix[4]arene substructures connected by aliphatic chains of various length (three to five carbon atoms) between two oppositep-positions and two distal phenolic oxygens have been synthesized. Starting withp-tert-butyl-calix[4]arene, two O-protected phenolic units are attachedvia ether links in 1,3-position by reaction with the corresponding tosylates. After deprotection, the new calix[4]arene is formed by fragment condensation with 2,6-bisbromomethylated 4-alkylphenols. The structure of one example (8c) has been confirmed by single crystal X-ray analysis. Both calixarene parts assume the cone conformation, a molecule of acetonitrile being included in both cavities.

Zusammenfassung

Neue makrotricyclische Verbindungen, in denen zwei Calix[4]aren-Einheiten durch aliphatische Ketten unterschiedlicher Länge (drei bis fünf C-Atome) zwischen zwei gegenüberliegendenp-Positionen und zwei gegenüberliegenden Phenolsauerstoffen verknüpft sind, wurden hergestellt. Ausgehend vonp-tert-Butyl-calix[4]aren werden zunächst zwei O-geschützte Phenolbausteine in 1,3-Stellung durch Umsetzung mit den entsprechenden Tosylaten etherartig gebunden. Nach Abspaltung der Benzylether-Schutzgruppe wird durch Fragmentkondensation mit 2,6-bisbrommethylierten 4-Alkylphenolen das neue Calix[4]aren gebildet. Für8c wurde die Struktur durch Einkristallröntgenstrukturanalyse bestätigt. Beide Calixarenteile nehmen diecone-Konformation ein, wobei in die beiden Hohlräume je ein Molekül Acetonitril eingeschlossen wird.

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Authors and Affiliations

  1. Faculty of Chemistry, Warsaw University of Technology, PL-00664, Warsaw, Poland

    W. Wąsikiewicz, G. Rokicki & J. Kiełkiewicz

  2. Hoechst AG, D-65926, Frankfurt/Main, Germany

    E. F. Paulus

  3. Institut für Organische Chemie, Johannes Gutenberg Universität, D-55099, Mainz, Germany

    V. Böhmer

Authors
  1. W. Wąsikiewicz
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  2. G. Rokicki
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  3. J. Kiełkiewicz
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  4. E. F. Paulus
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  5. V. Böhmer
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Wąsikiewicz, W., Rokicki, G., Kiełkiewicz, J. et al. Head-to-tail connected double calix[4]arenes. Monatsh Chem 128, 863–879 (1997). https://doi.org/10.1007/BF00807096

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  • DOI: https://doi.org/10.1007/BF00807096

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