Islam, Md Monarul, Akther, Thamina, Ikejiri, Yusuke, Matsumoto, Taisuke, Tanaka, Junji, Rahman, Shofiur, Georghiou, Paris E., Hughes, David L., Redshaw, Carl and Yamato, Takehiko (2016) Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans. RSC Advances, 6 (56). pp. 50808-50817. ISSN 2046-2069

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Abstract

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.

Item Type:	Article
Uncontrolled Keywords:	chemistry(all),chemical engineering(all) ,/dk/atira/pure/subjectarea/asjc/1600
Faculty \ School:	Faculty of Science > School of Chemistry
Related URLs:	http://www.scopus.com/inward/record.url?... https://hull-repository.worktribe.com/ou...
Depositing User:	LivePure Connector
Date Deposited:	30 Aug 2019 13:30
Last Modified:	22 Apr 2020 08:09
URI:	https://ueaeprints.uea.ac.uk/id/eprint/72067
DOI:	10.1039/c6ra06219a

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