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J Am Chem Soc. 2019 Sep 25;141(38):14955-14960. doi: 10.1021/jacs.9b06197. Epub 2019 Aug 22.

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

Author information

1
Department of Chemical Science and Engineering , Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8550 , Japan.
2
Department of Chemistry and Biological Science , Aoyama Gakuin University , Fuchinobe , Chuo-ku, Sagamihara , Kanagawa 252-5258 , Japan.
3
Graduate School of Pharmaceutical Sciences , The University of Tokyo , 7-3-1 Hongo , Bunkyo-ku, Tokyo 113-0033 , Japan.
4
Cluster for Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN , 2-1 Hirosawa Wako, Saitama 351-0198 , Japan.
5
Department of Chemistry , Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8550 , Japan.
6
Molecular Structure Characterization Unit, RIKEN Center for Sustainable Resource Science (CSRS) , 2-1 Hirosawa , Wako, Saitama 351-0198 , Japan.

Abstract

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.

PMID:
31418559
DOI:
10.1021/jacs.9b06197

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