Synthesis and Conformational Study of the First Triply Bridged Calix[6]azatubes

The first C 3 v - and D 3 h -symmetrical triply bridged calix[6]azatubes were prepared in good yields from the known 1,3,5-tris-methylated calix[6]arene through an efficient [1 + 1] macrocyclization reaction. A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substitut...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-02, Vol.70 (4), p.1204-1210
Main Authors: Le Gac, Stéphane, Zeng, Xianshun, Reinaud, Olivia, Jabin, Ivan
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
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Summary:The first C 3 v - and D 3 h -symmetrical triply bridged calix[6]azatubes were prepared in good yields from the known 1,3,5-tris-methylated calix[6]arene through an efficient [1 + 1] macrocyclization reaction. A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substituted at the wide rim in alternate position by tBu and nitro groups. A 1H NMR study showed that, whereas the parent bis-calix[6]arenes self-include their methoxy groups, thereby closing their inner tube, the nitro-substituted calix[6]azatube undergoes a conformational change with the expulsion of the methoxy groups, hence presenting a three-dimensional structure open for host−guest applications.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048137l