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

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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… Click to show full 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.

Keywords: deoxygenation oxygenation; synthesis symmetrical; regioselective deoxygenation; design synthesis

Journal Title: Organic letters
Year Published: 2022

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