The first synthesis and characterisation of elusive cone 1,2-diformyl tetralkoxycalix[4]arenes and their derivatives

A. Sartori, Alessandro Casnati, Luigi Mandolini, Francesco Sansone, David Reinhoudt

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    12 Citations (Scopus)

    Abstract

    The synthesis and isolation of elusive tetralkoxycalix[4]arenes 2 in the cone conformation and bearing two formyl groups in proximal (1,2) positions at the upper rim are described for the first time. They were obtained as a mixture with the distal (1,3) regioisomers 3 by optimizing the Gross formylation reaction on the tetralkoxycalix[4]arenes 1. After reduction to the corresponding alcohols, compounds 4 could be isolated and oxidized to 1,2-diformyl (2) and 1,2-diacid (6) tetralkoxycalix[4]arenes. These 1,2-difunctionalized derivatives are useful intermediates for the synthesis of calixarene-based molecular receptors having proximal binding groups.
    Original languageUndefined
    Pages (from-to)5539-5544
    Number of pages6
    JournalTetrahedron
    Volume59
    Issue number29
    DOIs
    Publication statusPublished - 2003

    Keywords

    • METIS-215635
    • IR-40882

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