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Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes

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

Authors

Thamina Akther

Md. Monarul Islam

Shofiur Rahman

Paris E. Georghiou

Taisuke Matsumoto

Junji Tanaka

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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

A series of syn- and anti-[2.n]metacyclophan-1-enes have been prepared in good yields by McMurry cyclizations of 1,n-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)alkanes. Significantly, acid catalyzed rearrangements of [2.n]metacyclophan-1-enes afforded [n.1]metacyclophanes in good yield. The ratios of the products are strongly regulated by the number of methylene bridges present. The percentages of the rearrangement products increase with increasing length of the carbon bridges. Characterization and the conformational studies of these products are described. Single crystal X-ray analysis revealed the adoption of syn- and anti-conformations. DFT calculations were carried out to estimate the energy-minimized structures of the synthesized metacyclophanes.

Publication Date Apr 28, 2017
Journal Organic & biomolecular chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 15
Issue 16
Pages 3519-3527
Institution Citation Akther, T., Islam, M. M., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., …Yamato, T. (2017). Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes. Organic & biomolecular chemistry, 15(16), 3519-3527. https://doi.org/10.1039/C7OB00400A
DOI https://doi.org/10.1039/C7OB00400A
Keywords Epoxides; Metacyclophanes
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB00400A#!divAbstract
Copyright Statement ©2018 University of Hull
Additional Information This is the accepted manuscript of an article published in Organic & biomolecular chemistry, 2017. The version of record is available at the DOI link in this record.

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