Selective Synthesis of [2]- and [3]Catenane Tuned by Ring Size and Concentration

The syntheses of [2]- and [3]­catenanes by olefin metathesis and oxidative acetylide coupling have been studied in detail. Pseudorotaxanes that were obtained by mixing crown ether and ammonium salts containing two terminal reactive end-groups were converted to [2]- and [3]­catenane. Their yields wer...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-06, Vol.78 (11), p.5205-5217
Main Authors: Iwamoto, Hajime, Takizawa, Wataru, Itoh, Koji, Hagiwara, Tatsuya, Tayama, Eiji, Hasegawa, Eietsu, Haino, Takeharu
Format: Article
Language:English
Subjects:
Catenanes - chemical synthesis
Catenanes - chemistry
Molecular Conformation
Particle Size
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Summary:The syntheses of [2]- and [3]­catenanes by olefin metathesis and oxidative acetylide coupling have been studied in detail. Pseudorotaxanes that were obtained by mixing crown ether and ammonium salts containing two terminal reactive end-groups were converted to [2]- and [3]­catenane. Their yields were influenced not only by the chain length of the ammonium salts but also by the concentration of the crown ether and the ammonium salts. The strain energies of [2]­catenane were responsible for the formation of [2]­catenane.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400239h