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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

Md Monarul Islam

Tomiyasu Hirotsugu

Pierre Thuery

Taisuke Matsumoto

Junji Tanaka

Mark R.J. Elsegood

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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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