Andrew Behrle - Synthesis of amine, halide, and pyridinium terminated 2-alkyl-p-tert-butylcalix[4]arene

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      Publication Details (including relevant citation   information):

      Referenced by:

      1. Fischer, C.; Guisheng, L.; Bombicz, P.; Seichter, W.; Weber,   E. Stuct. Chem. 2011, 22,   433-439.

      2. Itzhak, N.; Biali, S. Supramol. Chem.  2010, 22, 704-709.

      3. Itzhak, N.; Biali, S. J. Org. Chem.  2010, 75, 3437-3442.

      Abstract:

      The synthesis of calix[4]arenes with functional groups tethered   to a single methylene bridge has been explored. Mono-lithiated   calix[4]arenes react with 1,u-bromochloroalkanes to give   2-(u-chloroalkyl)-calix[4]arenes, which function as key   intermediates in the synthesis of a variety of   tether-functionalized calix[4]arenes. Subsequent reactivity of   these chloroalkyl species has allowed for successful synthesis of   2-(u-iodoalkyl)-calix[4]arenes,   2-(u-pyridiniumalkyl)-calix[4]arenes, and   2-(u-aminoalkyl)-calix[4] arenes. This latter group of   amine-terminated calix[4]arenes are especially significant as   they may serve as useful entries to a wide range of subsequent   chemistry, including metal coordination or attachment to a solid   support. Both alkyl and aryl amines have been incorporated at the   end of the tether, and a 2,6-

      diisopropylaniline derivative has been analyzed by X-ray   diffraction.

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