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Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes

Akther, Thamina; Islam, Md Monarul; Matsumoto, Taisuke; Tanaka, Junji; Feng, Xing; Redshaw, Carl; Yamato, Takehiko

Authors

Thamina Akther

Md Monarul Islam

Taisuke Matsumoto

Junji Tanaka

Xing Feng

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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

© 2016 Elsevier B.V. All rights reserved. Novel [n]benzofuranophanes (n = 8 & 10) 2a-b have been prepared by successive intramolecular cyclization from 5,19-di-tert-butyl-8,22-dimethoxy[n]metacyclophane-1-yne (syn-1a-b) by treatment with BBr 3 in CH 2 Cl 2 at room temperature for 8h. [2.n]Benzofuranophanes 2a-b were also obtained by treatment of 1,2-di-endo-bromo-5,19-di-tert-butyl-8,22-dimethoxy[n] metacyclophane (meso-3a-b) with BBr 3 in CH 2 Cl 2 by using the same reaction conditions. 1 H NMR spectra of 2a-b reveals the formation of intramolecular hydrogen bonding between hydroxyl proton with the oxygen of the furan moiety and X-ray analysis shows that the lengths between H (OH) and O (furan) are 1.981 and 1.823 Å, respectively. The conformation of [8]benzofuranophane 2a in solution is rigid with restricted rotation around the diaryl linkage rather than [10] benzofuranophane 2b because of weak intramolecular hydrogen bonding and the short length of the cross-linking chain.

Citation

Akther, T., Islam, M. M., Matsumoto, T., Tanaka, J., Feng, X., Redshaw, C., & Yamato, T. (2016). Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes. Journal of molecular structure, 1122(15 October), 247-255. https://doi.org/10.1016/j.molstruc.2016.05.054

Journal Article Type Article
Acceptance Date May 17, 2016
Online Publication Date May 24, 2016
Publication Date Oct 15, 2016
Deposit Date Jun 22, 2016
Publicly Available Date Mar 29, 2024
Journal Journal of molecular structure
Print ISSN 0022-2860
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 1122
Issue 15 October
Pages 247-255
DOI https://doi.org/10.1016/j.molstruc.2016.05.054
Keywords [2.n]metacyclophanes, Demethylation, [n]Benzofuranophanes, Intramolecular hydrogen bond
Public URL https://hull-repository.worktribe.com/output/440062
Publisher URL http://www.sciencedirect.com/science/article/pii/S0022286016305002
Additional Information This article is maintained by: Elsevier; Article Title: Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n]metacyclophane-1-ynes with BBr3 to afford novel [n]benzofuranophanes; Journal Title: Journal of Molecular Structure; CrossRef DOI link to publisher maintained version: http://dx.doi.org/10.1016/j.molstruc.2016.05.054; Content Type: article; Copyright: © 2016 Elsevier B.V. All rights reserved.

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