Synthesis and Application of New Triplet and Singlet Carbenes
| Project/Area Number |
26288017
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Hiroshima University |
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Principal Investigator |
Yamamoto Yohsuke 広島大学, 理学(系)研究科(研究院), 教授 (50158317)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000)
Fiscal Year 2016: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2015: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥6,760,000 (Direct Cost: ¥5,200,000、Indirect Cost: ¥1,560,000)
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| Keywords | カルベン / 合成 / 構造 / 反応中間体 / ESR / 性質 |
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| Outline of Final Research Achievements |
Triplet carbenes are very difficult to stabilize, and the synthesis of isolable triplet carbenes is a worthwhile challenge. Tomioka et al. have reported two long-living carbenes in solution. However, the isolation of triplet carbenes in the solid state still remains to be achieved.
Recently, we proposed a new strategy for the generation of triplet carbenes by two-electron oxidation of allenic precursors bearing two thioxanthene or acridene moieties. Oxidation of allenic compound bearing two diphenoxyacridene moieties resulted in a cyclized product and 3,5-ditBuphenoexy substituted system resulted in a stable singlet carbene after two electron oxidation. But we succeeded in preparation of sterically very rigid allene and the oxidation afforded the target triplet carbene. Although the triplet carbene was stable only at low temperatures, we could observe the characteristic ESR signals of the target triplet carbene.
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Report
(4 results)
Research Products
(103 results)
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[Journal Article] Isolation of Hypervalent Group-16 Radicals and Their Application in Organic-Radical Batteries.2016
Author(s)
Yasuyuki Imada, Hideyuki Nakano, Ko Furukawa, Ryohei Kishi, Masayoshi Nakano, Hitoshi Maruyama, Masaaki Nakamoto, Akira Sekiguchi, Masahiro Ogawa, Toshiaki Ohta, and Yohsuke Yamamoto
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Journal Title
Journal of American Chemical Society
Volume: 138
Issue: 2
Pages: 479-482
DOI
Related Report
Peer Reviewed
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[Presentation] Hypervalent pentacoordinated nirogen radical cations: Synthesis, structure, and application to singlet diradicaloid2015
Author(s)
Yohsuke Yamamoto, Masato Takeshita, Kaoko Sato, Junya Nakatsuji, Akihiro Kurosaki, Masayoshi Nakano, Ryohei Kishi, Ko Furukawa, Kenji Kamada
Organizer
THE INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES 2015
Place of Presentation
Honolulu（アメリカ）
Year and Date
2015-12-15
Related Report
Int'l Joint Research / Invited
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[Presentation] Toward synthesis of thermally stable triplet carbenes2015
Author(s)
Yohsuke Yamamoto, Junki Yamamoto, Shin-ichi Fuku-en, Ko Furukawa, Ryohei Kishi, Masayoshi Nakano
Organizer
THE INTERNATIONAL CHEMICAL CONGRESS OF PACIFIC BASIN SOCIETIES 2015
Place of Presentation
Honolulu（アメリカ）
Year and Date
2015-12-15
Related Report
Int'l Joint Research / Invited
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[Presentation] 溶解度の高い新規スフェランドの合成2015
Author(s)
和田 佳奈子, 桑名 祐里, 鈴川 直幸, 柏葉 崇, 松川 史郎, 箕浦 真生, 山本 陽介
Organizer
2015年日本化学会中国四国支部大会
Place of Presentation
岡山
Year and Date
2015-11-14
Related Report
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[Presentation] 新規一重項カルベンの合成検討2014
Author(s)
前田直人・山本純基・菅原峻・山本陽介
Organizer
2014年日本化学会中国四国支部大会
Place of Presentation
山口市
Year and Date
2014-11-08 – 2014-11-09
Related Report
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[Presentation] 安定な三重項カルベンの合成検討2014
Author(s)
山本純基, 福圓真一, 古川貢, 中野雅由, 岸亮平, 安倍学, 山本陽介
Organizer
第24回基礎有機化学討論会
Place of Presentation
仙台市
Year and Date
2014-09-07 – 2014-09-09
Related Report
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