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Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes
journal contributionposted on 2015-09-07, 10:29 authored by Md. Monarul Islam, Tomiyasu Hirotsugu, Pierre Thuery, Taisuke Matsumoto, Junji Tanaka, Mark ElsegoodMark Elsegood, Carl Redshaw, Takehiko Yamato
Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete "homocalixarene", has been prepared from rimethoxy[3.3.1]metacyclophane by demethylation with trimethylsilyl iodide in MeCN. Di-O-methylation at the lower rim of trihydroxy[3.3.1]metacyclophane in the presence of K2CO3 in acetone afforded a novel, inherently chiral calixarene-analogue, namely a macrocyclic [3.3.1]metacyclophane, possessing C1 symmetry. The inherent chirality of the two conformers was characterized by 1H NMR spectroscopy by addition of an excess of Pirkle's chiral shift reagent [(S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol], which caused a splitting of the OMe group and AB patterns corresponding to the methylene protons.
Published inJournal of Molecular Structure
Pages47 - 54
CitationISLAM, M.M. ...et al., 2015. Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes. Journal of Molecular Structure, 1098, pp. 47-54.
Publisher© 2015 Elsevier
- AM (Accepted Manuscript)
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