Thamina Akther
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
Md. Monarul Islam
Shofiur Rahman
Paris E. Georghiou
Taisuke Matsumoto
Junji Tanaka
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.
Citation
Akther, T., Islam, M. M., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., Redshaw, C., & 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
Acceptance Date | Mar 29, 2017 |
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Online Publication Date | Mar 31, 2017 |
Publication Date | Apr 28, 2017 |
Deposit Date | May 8, 2017 |
Publicly Available Date | Apr 3, 2018 |
Journal | Organic & biomolecular chemistry |
Print ISSN | 1477-0520 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 15 |
Issue | 16 |
Pages | 3519-3527 |
DOI | https://doi.org/10.1039/C7OB00400A |
Keywords | Epoxides; Metacyclophanes |
Public URL | https://hull-repository.worktribe.com/output/451155 |
Publisher URL | http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB00400A#!divAbstract |
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. |
Contract Date | Apr 3, 2018 |
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©2018 University of Hull
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