Design and Synthesis of a C3 Symmetrical Phenalenyl Derivative with Three Oxo Groups by Regioselective Deoxygenation/Oxygenation

Tsuyoshi Murata; Kenta Yoshida; Shuichi Suzuki; Akira Ueda; Shinsuke Nishida; Junya Kawai; Kozo Fukui; Kazuhiro Nakasuji; Yasushi Morita

doi:10.1021/acs.orglett.1c04227

Design and Synthesis of a C₃ Symmetrical Phenalenyl Derivative with Three Oxo Groups by Regioselective Deoxygenation/Oxygenation

Org Lett. 2022 Feb 4;24(4):1033-1037. doi: 10.1021/acs.orglett.1c04227. Epub 2022 Jan 20.

Authors

Tsuyoshi Murata¹, Kenta Yoshida², Shuichi Suzuki³, Akira Ueda⁴, Shinsuke Nishida¹, Junya Kawai², Kozo Fukui², Kazuhiro Nakasuji², Yasushi Morita¹

Affiliations

¹ Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, Yachigusa 1247, Yakusa, Toyota, Aichi 470-0392, Japan.
² Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.
³ Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
⁴ Department of Chemistry, Kumamoto University, Chuo-ku, Kumamoto 860-8555, Japan.

PMID: 35050630
DOI: 10.1021/acs.orglett.1c04227

Abstract

Tri-tert-butylated 4,7-dihydroxyphenalenone was designed and synthesized from a corresponding 4,9-dimethoxyphenalenone derivative by regioselective deoxygenation/oxygenation. The 4,7-dihydroxyphenalenone derivative showed a chromic behavior accompanied by protonation and deprotonation, giving monocation and dianion species, respectively, and their C₃ symmetric electronic structures were elucidated by experimental and theoretical methods.