TY - JOUR
T1 - Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes
AU - Islam, Md Monarul
AU - Hirotsugu, Tomiyasu
AU - Thuery, Pierre
AU - Matsumoto, Taisuke
AU - Tanaka, Junji
AU - Elsegood, Mark R.J.
AU - Redshaw, Carl
AU - Yamato, Takehiko
N1 - Funding Information:
We would like to thank the OTEC at Saga University for financial support. This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)” CR thanks the EPSRC for a travel award.
Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.
PY - 2015/6/12
Y1 - 2015/6/12
N2 - Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete "homocalix[3]arene", has been prepared from trimethoxy[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.
AB - Trihydroxy[3.3.1]metacyclophane, which can be regarded as an unsymmetrical or incomplete "homocalix[3]arene", has been prepared from trimethoxy[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.
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U2 - 10.1016/j.molstruc.2015.05.036
DO - 10.1016/j.molstruc.2015.05.036
M3 - Article
AN - SCOPUS:84930934301
SN - 0022-2860
VL - 1098
SP - 47
EP - 54
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -