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

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.

SUBMITTER: Fischer C

PROVIDER: S-EPMC3252863 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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

Fischer Conrad C Seichter Wilhelm W Weber Edwin E

Beilstein journal of organic chemistry 20111130

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 respec ...[more]

PMID: 22238537

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