Issue 22, 2015
From the journal:

Chemical Communications

Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene†

Takashi Matsuno,a   Yutaro Koyama,a   Satoru Hiroto,*a   Jatish Kumar,b   Tsuyoshi Kawaib  and  Hiroshi Shinokubo*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan
E-mail: hshino@apchem.nagoya-u.ac.jp, hiroto@apchem.nagoya-u.ac.jp

b Graduate School of Material Science, Nara Institute of Science and Technology (NAIST), Ikoma, Japan

Abstract

Oxidation of 2-hydroxy-9,10-dialkynylanthracenes resulted in highly regioselective dimerization to furnish metastable dearomatized 1,4-diketones rather than stable aromatic diols. The 1,4-diketones were converted to oxahelicenes, which exhibited strong fluorescence both in solution and solid state as well as chiroptical properties.

Graphical abstract: Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene

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Article information

DOI
https://doi.org/10.1039/C5CC00764J
Article type
Communication
Submitted
27 Jan 2015
Accepted
09 Feb 2015
First published
09 Feb 2015
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2015,51, 4607-4610

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Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene

T. Matsuno, Y. Koyama, S. Hiroto, J. Kumar, T. Kawai and H. Shinokubo, Chem. Commun., 2015, 51, 4607 DOI: 10.1039/C5CC00764J

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