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Title: Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes
Authors: Islam, Md. Monarul
Hirotsugu, Tomiyasu
Thuery, Pierre
Matsumoto, Taisuke
Tanaka, Junji
Elsegood, Mark R.J.
Redshaw, Carl
Yamato, Takehiko
Keywords: Metacyclophanes
Macrocycles
Calixarenes
Intramolecular hydrogen bonding
Oemethylation
Chirality
Issue Date: 2015
Publisher: © 2015 Elsevier
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.
Abstract: 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 K<inf>2</inf>CO<inf>3</inf> in acetone afforded a novel, inherently chiral calixarene-analogue, namely a macrocyclic [3.3.1]metacyclophane, possessing C<inf>1</inf> symmetry. The inherent chirality of the two conformers was characterized by <sup>1</sup>H 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.
Description: This paper is in closed access
Version: Accepted for publication
DOI: 10.1016/j.molstruc.2015.05.036
URI: https://dspace.lboro.ac.uk/2134/18636
Publisher Link: http://dx.doi.org/10.1016/j.molstruc.2015.05.036
ISSN: 0022-2860
Appears in Collections:Closed Access (Chemistry)

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