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Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans

Islam, Md Monarul; Akther, Thamina; Ikejiri, Yusuke; Matsumoto, Taisuke; Tanaka, Junji; Rahman, Shofiur; Georghiou, Paris E.; Hughes, David L.; Redshaw, Carl; Yamato, Takehiko


Md Monarul Islam

Thamina Akther

Yusuke Ikejiri

Taisuke Matsumoto

Junji Tanaka

Shofiur Rahman

Paris E. Georghiou

David L. Hughes

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Professor Carl Redshaw
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Takehiko Yamato


Calix[3]benzofurans have been synthesized by a modified TosMIC coupling reaction, followed by acid treatment and an intramolecular cyclization reaction with TMSI (trimethylsilyl iodide); X-ray analysis established the structures of two samples, both showing a cone conformation. 1H NMR spectroscopic analyses of the calix[3]benzofurans reveal that they can adopt drastically different conformations in solution and undergo very fast conformational changes relative to the NMR time scale. Calix[3]benzofuran 4a exists as two conformers, namely the cone and saddle forms, in a ratio of 83 : 17 at −50 °C. A series of calix[3]benzofuran derivatives was synthesized by electrophilic aromatic substitutions, such as bromination, formylation and acylation, to investigate the influence of the substituents on the conformations of the calix[3]benzofurans. 1H NMR spectral analyses of the acyl derivatives at room temperature indicated that these macrocycles exist as a mixture of two isomers that are slowly interconverted on the 1H NMR timescale. The conformational isomers of the calix[3]benzofurans and their derivatives obtained from DFT methods (based on the crystal structure analysis results) were used to estimate the total energies of the different conformations.


Islam, M. M., Akther, T., Ikejiri, Y., Matsumoto, T., Tanaka, J., Rahman, S., …Yamato, T. (in press). Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans. RSC advances, 6(56), 50808-50817.

Journal Article Type Article
Acceptance Date May 16, 2016
Online Publication Date May 18, 2016
Deposit Date Jun 21, 2016
Publicly Available Date Jun 21, 2016
Journal RSC advances
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 6
Issue 56
Pages 50808-50817
Keywords Calix[3]benzofurans
Public URL
Publisher URL!divAbstract
Additional Information : This document is Similarity Check deposited; : Supplementary Information; : Crystal Structure Data; : The Royal Society of Chemistry has an exclusive publication licence for this journal; : Single-blind; : Received 9 March 2016; Accepted 16 May 2016; Accepted Manuscript published 18 May 2016; Version of Record published 24 May 2016


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