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|Title: ||Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes|
|Authors: ||Islam, Md. Monarul|
Elsegood, Mark R.J.
Intramolecular hydrogen bonding
|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 "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 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|
|Publisher Link: ||http://dx.doi.org/10.1016/j.molstruc.2015.05.036|
|Appears in Collections:||Closed Access (Chemistry)|
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