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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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