かさ高いシリル基を有するジベンゾペンタレンの酸化・還元反応

橋本 陽子; 斎藤 雅一

doi:10.11494/kisoyuki.2008.0.21.0

19th Symposium on Fundamental Organic Chemistry

Session ID : 1P021

DOI https://doi.org/10.11494/kisoyuki.2008.0.21.0

Conference information

Host: Organizing Committee of Symposium on Fundamental Organic Chemistry

Co-host: The Chemical Society of Japan, The Kinki Chemical Society, Japan, Osaka University Global COE Program "Global Education and Research Center for Bio-Environmental Chemistry", The Society of Synthetic Organic Chemistry, Japan, The Pharmaceutical Society of Japan

Poster Presentation

Redox Reactions of a Dibenzopentalene Having Bulky Silyl Substituents

*Yoko Hashimoto, Masaichi Saito

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Keywords: Dibenzopentalene, Oxidation, Reduction

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Abstract

We examined redox reactions of a novel dibenzopentalene 1, synthesized by reduction of phenylacetylene having a bulky silyl substituent followed by oxidation of the resulting dilithium dibenzopentalenide 3. After treatment of 1 with oxidants (NO⁺SbF₆^-, SbCl₅ and SbF₅), ESR signals were observed in each of reaction mixtures, suggesting generation of cation radical 2. On the other hand, reduction of 1 with excess lithium gave dilithium dibenzopentalenide 3 in 81% yield. After treatment of 1 with an equivalent of KC₈, an ESR signal was observed, suggesting generation of anion radical 4. Reactions of 3 with a variety of metal reagents were also examined.

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