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"Syn effect" in nucleophilic addition of amines to 1,3-dienyl sulfone and ethyl (E)-2,4-pentadienoate
https://doi.org/10.24517/00010668
https://doi.org/10.24517/00010668739296d4-b3bc-438b-8b07-bd7b63888870
| 名前 / ファイル | ライセンス | アクション |
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SC-PR-YAMAZAKI-M-740.pdf (319.4 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||||||
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| 公開日 | 2017-10-03 | |||||||||
| タイトル | ||||||||||
| タイトル | "Syn effect" in nucleophilic addition of amines to 1,3-dienyl sulfone and ethyl (E)-2,4-pentadienoate | |||||||||
| 言語 | en | |||||||||
| 言語 | ||||||||||
| 言語 | eng | |||||||||
| 資源タイプ | ||||||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||||||
| 資源タイプ | journal article | |||||||||
| ID登録 | ||||||||||
| ID登録 | 10.24517/00010668 | |||||||||
| ID登録タイプ | JaLC | |||||||||
| 著者 |
Yamazaki, Masao
× Yamazaki, Masao× Guha, Samar Kumar× Ukaji, Yutaka× Inomata, Katsuhiako |
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| 著者別表示 |
宇梶, 裕
× 宇梶, 裕
× 猪股, 勝彦
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| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 81, 号 6, p. 740-753, 発行日 2008-01-01 |
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| ISSN | ||||||||||
| 収録物識別子タイプ | ISSN | |||||||||
| 収録物識別子 | 0009-2673 | |||||||||
| NCID | ||||||||||
| 収録物識別子タイプ | NCID | |||||||||
| 収録物識別子 | AA00580132 | |||||||||
| 出版者 | ||||||||||
| 出版者 | The Chemical Society of Japan = 日本化学会 | |||||||||
| 抄録 | ||||||||||
| 内容記述タイプ | Abstract | |||||||||
| 内容記述 | The stereochemistry of nucleophilic addition of amines to (E)-1-tosyl-1,3-butadiene was investigated. The Z/E ratios of the resulting allylic sulfones varied with amines, solvents, temperature, and concentration. When diethylamine was reacted in low concentration at high temperature, the corresponding sterically unfavorable (Z)-4-amino-2-butenyl sulfone was preferentially obtained. The stereochemistry of nucleophilic addition of amines to ethyl (E)-2,4-pentadienoate, which possesses an ester group as a conjugated electron-withdrawing group instead of a p-toluenesulfonyl (Ts) group, was also found to realize similar high Z selectivity. The predominant formation of Z isomers in both cases was rationalized by a “syn effect,” which might be mainly due to n⁄σ→π* interaction and/or 6π-electron homoaromaticity. | |||||||||
| 権利 | ||||||||||
| 権利情報 | Copyright © The Chemical Society of Japan 日本化学会 | |||||||||
| 著者版フラグ | ||||||||||
| 出版タイプ | VoR | |||||||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||||||
| 関連URI | ||||||||||
| 関連タイプ | isVersionOf | |||||||||
| 識別子タイプ | DOI | |||||||||
| 関連識別子 | https://doi.org/10.1246/bcsj.81.740 | |||||||||
| 関連URI | ||||||||||
| 関連タイプ | isIdenticalTo | |||||||||
| 識別子タイプ | URI | |||||||||
| 関連識別子 | https://www.jstage.jst.go.jp/browse/bcsj | |||||||||
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| 関連タイプ | isIdenticalTo | |||||||||
| 識別子タイプ | URI | |||||||||
| 関連識別子 | http://www.chemistry.or.jp/ | |||||||||
