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

Shuhei Nishigaki, Yu Shibata, Atsuya Nakajima, Hajime Okajima, Yui Masumoto, Taisei Osawa, Atsuya Muranaka, Haruki Sugiyama, Ayano Horikawa, Hidehiro Uekusa, Hiroyuki Koshino, Masanobu Uchiyama, Akira Sakamoto, Ken Tanaka

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)14955-14960
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number38
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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