Stereochemical Study on 1,3-Dipolar Cycloaddition Reactions of Heteroaromatic <i>N</i>-Ylides with Symmetrically Substituted cis and trans Olefins
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- Tsuge Otohiko
- Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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- Kanemasa Shuji
- Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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- Takenaka Shigeori
- Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
書誌事項
- タイトル別名
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- Stereochemical study on 1,3-dipolar cycloaddition reactions of heteroaromatic N-ylides with symmetrically substituted cis and trans olefins.
抄録
Stereochemistry of the cycloadditions of twenty-four heteroaromatic N-ylides with several symmetrically substituted cis and trans olefins has been investigated. Cyclic and acyclic cis olefins cycloadd to the and form of the ylides in a highly endo-selective manner giving almost quantitative yields of stereospecific endo 3+2 cycloadducts. N-Ylides stabilized with a substituent of carbonyl type react with trans olefins to form mostly two stereoisomeric 3+2 cycloadducts to the anti form of the ylides. In most cases, they undergo the stereospecific interconversion through a retro cycloaddition process, the isomer ratios and the easiness of transformation depending upon the nature and size of substituents on the five-membered ring which has been built up in the cycloaddition step. On the other hand, N-ylides stabilized with a substituent of noncarbonyl type react with trans olefins to give stereospecific and stereoselective 3+2 cycloadducts as single isomers which are assigned as the cycloadducts to the syn form of the ylides.
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 58 (11), 3137-3157, 1985
公益社団法人 日本化学会
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詳細情報 詳細情報について
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- CRID
- 1390001204128554880
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- NII論文ID
- 130001984076
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- ISSN
- 13480634
- 00092673
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可