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

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

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Published inJournal of the American Chemical Society Vol. 141; no. 38; pp. 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 Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 25.09.2019
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
AROMATICITY
NUMBER
EXPANDED PORPHYRIN
COMPLEXES
REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION
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Summary:A belt-shaped [8] cycloparaphenylene (CPP) and an enantioenriched Mobius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Mobius-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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06197