Md Monarul Islam
Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes
Islam, Md Monarul; Hirotsugu, Tomiyasu; Thuery, Pierre; Matsumoto, Taisuke; Tanaka, Junji; Elsegood, Mark R.J.; Redshaw, Carl; Yamato, Takehiko
Authors
Tomiyasu Hirotsugu
Pierre Thuery
Taisuke Matsumoto
Junji Tanaka
Mark R.J. Elsegood
Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry
Takehiko Yamato
Abstract
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.
Citation
Islam, M. M., Hirotsugu, T., Thuery, P., Matsumoto, T., Tanaka, J., Elsegood, M. R., …Yamato, T. (2015). Synthesis and conformational studies of calixarene analogue chiral [3.3.1]metacyclophanes. Journal of molecular structure, 1098, 47-54. https://doi.org/10.1016/j.molstruc.2015.05.036
Journal Article Type | Article |
---|---|
Acceptance Date | May 28, 2015 |
Online Publication Date | May 30, 2015 |
Publication Date | Sep 15, 2015 |
Deposit Date | Mar 15, 2016 |
Publicly Available Date | Mar 29, 2024 |
Journal | Journal of molecular structure |
Print ISSN | 0022-2860 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 1098 |
Pages | 47-54 |
DOI | https://doi.org/10.1016/j.molstruc.2015.05.036 |
Keywords | Metacyclophanes, Macrocycles, Calixarenes, Intramolecular hydrogen bonding, O–methylation, Chirality |
Public URL | https://hull-repository.worktribe.com/output/471887 |
Publisher URL | http://www.sciencedirect.com/science/article/pii/S002228601530020X |
Additional Information | Authors' accepted manuscript of article published in: Journal of molecular structure, 2015, v.1098 |
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Copyright Statement
© 2015, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
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