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Synthesis and Structures of [2.n]Metacyclophan-1-enes and their Conversion to Highly Strained [2.n]Metacyclophane-1-ynes

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

Authors

Thamina Akther

Md. Monarul Islam

Zannatul Kowser

Taisuke Matsumoto

Junji Tanaka

Shofiur Rahman

Abdullah Alodhayb

Paris E. Georghiou

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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

Syn-[2.n]metacyclophan-1-enes (n=5, 6, 8) are synthesized by the McMurry cyclization of 1,n-bis(3-formyl-4-methoxyphenyl)alkanes in good yields. Syn-[2.n]metacyclophan-1-enes (n= 6, 8) were converted to the highly strained syn-type [2.n] metacyclophane-1-ynes by successive bromination followed by dehydrobromination with KOBut. The attempted trapping reaction of [2.5]metacyclophane-1-yne by a Diels-Alder reaction with 1,3-diphenylisobenzofuran failed due to its smaller ring size and strained structure. The triple bonds in syn-[2.n]metacyclophane-1-ynes (n= 6,8) are distorted from linearity with the bond angles, 156.7° and 161.4° as shown by X-ray crystallographic analyses. A DFT (Density Functional Theory) computational study of the synthesized compounds was conducted to determine the stability of the different configurations.

Citation

Islam, M. M., Akther, T., Islam, M. M., Kowser, Z., Matsumoto, T., Tanaka, J., …Yamato, T. (2020). Synthesis and Structures of [2.n]Metacyclophan-1-enes and their Conversion to Highly Strained [2.n]Metacyclophane-1-ynes. European Journal of Organic Chemistry, 2020(27), 4167-4175. https://doi.org/10.1002/ejoc.202000548

Journal Article Type Article
Acceptance Date Jun 17, 2020
Online Publication Date Jun 17, 2020
Publication Date Jul 23, 2020
Deposit Date Jun 17, 2020
Publicly Available Date Jun 18, 2021
Journal European Journal of Organic Chemistry
Print ISSN 1434-193x
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2020
Issue 27
Pages 4167-4175
DOI https://doi.org/10.1002/ejoc.202000548
Keywords [2.n]metacyclophan-1-ynes; Structures; strained molecule; Diels-Alder reaction; Conformational studies
Public URL https://hull-repository.worktribe.com/output/3523176
Publisher URL https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202000548