Issue 22, 2015

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

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

Supplementary files

Article information

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

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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