Structural conditions required for the bridge lithiation and substitution of a basic calix[4]arene

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Abstract

Lithiation and subsequent reaction with CO 2 was applied to calix[4]arenes with different, equal or mixed, ether functions at the lower-rim site as well as tert-butylated or non-tert-butylated upper-rim positions. Whereas this reaction fails for symmetric calix[4]arene ethers with alkoxy residues greater than methoxy, the carboxylation of mixed methoxy-propoxy calixarene ethers is possible. In connection with this, several new monobridge-substituted calix[4]arenes were characterized with respect to their conformational behaviour in solution and the X-ray crystal structure of one key intermediate is taken into consideration. © 2011 Fischer et al; licensee Beilstein-Institut.

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Fischer, C., Seichter, W., & Weber, E. (2011). Structural conditions required for the bridge lithiation and substitution of a basic calix[4]arene. Beilstein Journal of Organic Chemistry, 7, 1602–1608. https://doi.org/10.3762/bjoc.7.188

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