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
Md. Monarul Islam
Paris E. Georghiou
Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry
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.
|Journal Article Type||Article|
|Journal||European Journal of Organic Chemistry|
|Peer Reviewed||Peer Reviewed|
|APA6 Citation||Akther, T., Islam, M. M., Kowser, Z., Matsumoto, T., Tanaka, J., Rahman, S., …Yamato, T. (in press). 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, https://doi.org/10.1002/ejoc.202000548|
|Keywords||[2.n]metacyclophan-1-ynes; Structures; strained molecule; Diels-Alder reaction; Conformational studies|
This file is under embargo until Jun 18, 2021 due to copyright reasons.
Contact C.Redshaw@hull.ac.uk to request a copy for personal use.
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