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

Takashi Matsuno; Yutaro Koyama; Satoru Hiroto; Jatish Kumar; Tsuyoshi Kawai; Hiroshi Shinokubo

doi:10.1039/c5cc00764j

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

Chem Commun (Camb). 2015 Mar 18;51(22):4607-10. doi: 10.1039/c5cc00764j.

Authors

Takashi Matsuno¹, Yutaro Koyama, Satoru Hiroto, Jatish Kumar, Tsuyoshi Kawai, Hiroshi Shinokubo

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan. hshino@apchem.nagoya-u.ac.jp hiroto@apchem.nagoya-u.ac.jp.

PMID: 25687191
DOI: 10.1039/c5cc00764j

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.