Publication Details (including relevant citation information):
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.
The synthesis of calixarenes with functional groups tethered to a single methylene bridge has been explored. Mono-lithiated calixarenes react with 1,u-bromochloroalkanes to give 2-(u-chloroalkyl)-calixarenes, which function as key intermediates in the synthesis of a variety of tether-functionalized calixarenes. Subsequent reactivity of these chloroalkyl species has allowed for successful synthesis of 2-(u-iodoalkyl)-calixarenes, 2-(u-pyridiniumalkyl)-calixarenes, and 2-(u-aminoalkyl)-calix arenes. This latter group of amine-terminated calixarenes 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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