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Synthesis and properties of bowl-shaped homotriazacalix[3 and 6] arenes and the acyclic analogues

✍ Scribed by Kazuaki Ito; Tomokazu Sato; Yoshihiro Ohba

Book ID: 102339965
Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 110 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400110

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✦ Synopsis

Abstract

Bowl‐shaped chiral homotriazacalixarenes were prepared by the cyclization reactions of chiral triamines with three equimolar amounts of bis(chloromethyl) phenols or bis(chloromethyl) phenol‐formaldehyde dimers in moderate yields. The corresponding acyclic phenol‐formaldehyde oligomers were also synthesized. The structural analysis of the macrocycles by nmr and circular dichroism spectra imply the existence of chiral transmission from the point chirality of the cysteine bridge to the cyclophane moiety. Their cyclic and acyclic compounds have a π‐base cavity large enough to include the ammonium ion.

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