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Synthesis of 1,3-Bis(tetracyano-2-azulenyl-3-butadienyl)azulenes by the [2+2] Cycloaddition-Retroelectrocyclization of 1,3-Bis(azulenylethynyl)azulenes with Tetracyanoethylene
http://hdl.handle.net/10091/00020643
http://hdl.handle.net/10091/00020643b8d2f17e-ff88-4ee7-a2f2-6f46a890646e
| 名前 / ファイル | ライセンス | アクション |
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Chem_Eur_J_20_11903-11912.pdf (461.2 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||||||||||||||
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| 公開日 | 2018-06-13 | |||||||||||||||||
| タイトル | ||||||||||||||||||
| タイトル | Synthesis of 1,3-Bis(tetracyano-2-azulenyl-3-butadienyl)azulenes by the [2+2] Cycloaddition-Retroelectrocyclization of 1,3-Bis(azulenylethynyl)azulenes with Tetracyanoethylene | |||||||||||||||||
| 言語 | ||||||||||||||||||
| 言語 | eng | |||||||||||||||||
| DOI | ||||||||||||||||||
| 関連識別子 | https://doi.org/10.1002/chem.201402939 | |||||||||||||||||
| 関連名称 | 10.1002/chem.201402939 | |||||||||||||||||
| キーワード | ||||||||||||||||||
| 主題 | azulene, cycloadditions, donor-acceptor system, electrochemistry, redox chemistry | |||||||||||||||||
| 資源タイプ | ||||||||||||||||||
| 資源 | http://purl.org/coar/resource_type/c_6501 | |||||||||||||||||
| タイプ | journal article | |||||||||||||||||
| 著者 |
Shoji, Taku
× Shoji, Taku
× Maruyama, Mitsuhisa
× Maruyama, Akifumi
× Ito, Shunji
× Okujima, Tetsuo
× Toyota, Kozo
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| 信州大学研究者総覧へのリンク | ||||||||||||||||||
| 氏名 | Shoji, Taku | |||||||||||||||||
| URL | http://soar-rd.shinshu-u.ac.jp/profile/ja.gmShOakh.html | |||||||||||||||||
| 出版者 | ||||||||||||||||||
| 出版者 | WILEY-V C H VERLAG GMBH | |||||||||||||||||
| 引用 | ||||||||||||||||||
| 内容記述 | CHEMISTRY-A EUROPEAN JOURNAL. 15(18):11903-11912 (2014) | |||||||||||||||||
| 書誌情報 |
CHEMISTRY-A EUROPEAN JOURNAL 巻 20, 号 37, p. 11903-11912, 発行日 2014-09-08 |
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| 抄録 | ||||||||||||||||||
| 内容記述 | 1,3-Bis(azulenylethynyl)azulene derivatives 9-14 have been prepared by palladium-catalyzed alkynylation of 1-ethynylazulene 8 with 1,3-diiodoazulene 1 or 1,3-diethynylazulene 2 with the corresponding haloazulenes 3-7 under Sonogashira-Hagihara conditions. Bis(alkynes) 9-14 reacted with tetracyanoethylene (TCNE) in a formal [2+2] cycloaddition-retroelectrocyclization reaction to afford the corresponding new bis(tetracyanobutadiene)s (bis(TCBDs)) 15-20 in excellent yields. The redox behavior of bis(TCBD)s 15-20 was examined by using CV and differential pulse voltammetry (DPV), which revealed their reversible multistage reduction properties under the electrochemical conditions. Moreover, a significant color change of alkynes 9-14 and TCBDs 15-20 was observed by visible spectroscopy under the electrochemical reduction conditions. | |||||||||||||||||
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| 収録物識別子タイプ | ISSN | |||||||||||||||||
| 収録物識別子 | 0947-6539 | |||||||||||||||||
| 書誌レコードID | ||||||||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||||||||
| 収録物識別子 | AA11076269 | |||||||||||||||||
| PubMed | ||||||||||||||||||
| 識別子タイプ | PMID | |||||||||||||||||
| 関連識別子 | http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?CMD=search&DB=pubmed&term=25098400 | |||||||||||||||||
| 関連名称 | 25098400 | |||||||||||||||||
| 権利 | ||||||||||||||||||
| 権利情報 | This is the peer reviewed version of the following article: Shoji, T. , Maruyama, M. , Maruyama, A. , Ito, S. , Okujima, T. and Toyota, K. (2014), Synthesis of 1,3‐Bis(tetracyano‐2‐azulenyl‐3‐butadienyl)azulenes by the [2+2] Cycloaddition–Retroelectrocyclization of 1,3‐Bis(azulenylethynyl)azulenes with Tetracyanoethylene. Chem. Eur. J., 20: 11903-11912. doi:10.1002/chem.201402939, which has been published in final form at |https://doi.org/10.1002/chem.201402939 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. | |||||||||||||||||
| 出版タイプ | ||||||||||||||||||
| 出版タイプ | AM | |||||||||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||||||||||
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| URL | http://gateway.isiknowledge.com/gateway/Gateway.cgi?&GWVersion=2&SrcAuth=ShinshuUniv&SrcApp=ShinshuUniv&DestLinkType=FullRecord&DestApp=WOS&KeyUT=000341630500039 | |||||||||||||||||
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Shoji, Taku, Maruyama, Mitsuhisa, Maruyama, Akifumi, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo, 2014, Synthesis of 1,3-Bis(tetracyano-2-azulenyl-3-butadienyl)azulenes by the [2+2] Cycloaddition-Retroelectrocyclization of 1,3-Bis(azulenylethynyl)azulenes with Tetracyanoethylene: WILEY-V C H VERLAG GMBH, 11903–11912 p.
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