Synthesis of sterically congested double helicene by alkyne cycloisomerization.

Autor: Hirano J; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp., Miyoshi S; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp., Yashima E; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp., Ikai T; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp.; PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama 332-0012, Japan., Shinokubo H; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp.; Integrated Research Consortium on Chemical Science (IRCCS), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan., Fukui N; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan. fukui@chembio.nagoya-u.ac.jp.; PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama 332-0012, Japan.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Jun 06; Vol. 60 (47), pp. 6035-6038. Date of Electronic Publication: 2024 Jun 06.
DOI: 10.1039/d4cc01573h
Abstrakt: Alkyne cycloisomerization of 2,7,10,15-tetra( ortho -alkynylphenyl)benzo[ g , p ]chrysene containing bulky 4-alkoxy-2,6-dimethylphenyl groups at the alkyne terminals selectively proceeded at the sterically crowded bay-region. The obtained double helicene adopts a distorted structure with a high racemization barrier due to the intramolecular steric repulsion.
Databáze: MEDLINE