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

Chem Commun (Camb)

Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.

Published: March 2015

AI Article Synopsis

  • The oxidation of 2-hydroxy-9,10-dialkynylanthracenes leads to a selective dimerization, producing metastable 1,4-diketones instead of stable aromatic diols.
  • The resulting 1,4-diketones can be transformed into oxahelicenes.
  • These oxahelicenes show strong fluorescence in both solution and solid forms, along with notable chiroptical properties.

Article 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.

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Source
http://dx.doi.org/10.1039/c5cc00764jDOI Listing

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