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| ファイル | 記述 | サイズ | フォーマット | |
|---|---|---|---|---|
| chem.202101735.pdf | 2.25 MB | Adobe PDF | 見る/開く |
| タイトル: | Mechanistic Investigation of a Synthetic Route to Biaryls by the Sigmatropic Rearrangement of Arylsulfonium Species |
| 著者: | Yanagi, Tomoyuki Yorimitsu, Hideki    https://orcid.org/0000-0002-0153-1888 (unconfirmed) |
| 著者名の別形: | 柳, 智征 依光, 英樹 |
| キーワード: | aryl sulfoxide DFT calculations mechanisms phenol sigmatropic rearrangement |
| 発行日: | Sep-2021 |
| 出版者: | Wiley |
| 誌名: | Chemistry – A European Journal |
| 巻: | 27 |
| 号: | 53 |
| 開始ページ: | 13450 |
| 終了ページ: | 13456 |
| 抄録: | A comprehensive mechanistic investigation was conducted on the coupling reaction of aryl sulfoxides with phenols by means of trif luoroacetic anhydride to yield biaryls. NMR experiments revealed that our previously proposed mechanism, which consists of a cascade of an interrupted Pummerer reaction and a rate-determining [3, 3] sigmatropic rearrangement, is reasonable. The electronic ef fects of the substrates have also been evaluated to elucidate the nature of the rearrangement step. Based on experimental observations and theoretical calculations, w e conclude that the rearrangement is highly asynchronous and stepwise rather than concerted when electron-rich phenols are employed for the reaction. |
| 著作権等: | This is the peer reviewed version of the following article: [T. Yanagi, H. Yorimitsu, Chem. Eur. J. 2021, 27, 13450.], which has been published in final form at https://doi.org/10.1002/chem.202101735. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. The full-text file will be made open to the public on 19 August 2022 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
| URI: | http://hdl.handle.net/2433/268765 |
| DOI(出版社版): | 10.1002/chem.202101735 |
| PubMed ID: | 34322930 |
| 出現コレクション: | 学術雑誌掲載論文等 |
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