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Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes

journal contribution
posted on 07.09.2015 by Md. Monarul Islam, Tomiyasu Hirotsugu, Pierre Thuery, Taisuke Matsumoto, Junji Tanaka, Mark Elsegood, Carl Redshaw, Takehiko Yamato
Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete "homocalix[3]arene", 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.

History

School

  • Science

Department

  • Chemistry

Published in

Journal of Molecular Structure

Volume

1098

Pages

47 - 54

Citation

ISLAM, 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

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2015

Notes

This paper is in closed access

ISSN

0022-2860

Language

en

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