Synthesis of Belt- and Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization

A belt-shaped [8]cycloparaphenylene (CPP) and an enantioenriched Möbius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Möbius-shaped [10]CPP possesses stable chirality and isolate...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-09, Vol.141 (38), p.14955-14960
Main Authors: Nishigaki, Shuhei, Shibata, Yu, Nakajima, Atsuya, Okajima, Hajime, Masumoto, Yui, Osawa, Taisei, Muranaka, Atsuya, Sugiyama, Haruki, Horikawa, Ayano, Uekusa, Hidehiro, Koshino, Hiroyuki, Uchiyama, Masanobu, Sakamoto, Akira, Tanaka, Ken
Format: Article
Language:English
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Summary:A belt-shaped [8]cycloparaphenylene (CPP) and an enantioenriched Möbius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Möbius-shaped [10]CPP possesses stable chirality and isolated with high enantiomeric purity. It is evident from the reaction Gibbs energy calculation that the above irreversible cyclotrimerizations are highly exothermic; therefore establishing that the intramolecular alkyne cyclotrimerization is a powerful route to strained cyclic molecular strips.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06197