書誌事項
- タイトル別名
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- Cyclization and Ring Transformation via Spirocyclic Arenium Ions
- スピロガタ アレーニウムイオン オ ケイユ スル カンカ ハンノウ オヨビ コッカク ヘンカン ハンノウ
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Our cyclizations and ring transformations via two types of spirocyclic arenium ions are described in this article. A spiro [5.2] octadienyl cation, which is well known as a Cram’s arenium ion, has attracted considerable attention in the aspect from physical organic chemistry. Our effort to utilize the intermediate as a synthetic tool resulted in the development of a lactonization of β-aryltosylate with an internal ester, a lactone ring transformation, and an ether ring transformation via the Cram’s arenium ion. We also developed a 7-endo selective Friedel-Crafts cyclization of various epoxy unsaturated esters promoted by Lewis acids. Detailed experimental data showed that a spiro [5.5] undecadienyl cation is a key intermediate of this reaction. The reaction mechanism seems to involve ipso-cyclization and subsequent skeletal rearrangement of the resulting spirocyclic arenium ion. The Friedel-Crafts cyclization was also applied to the formation of tetrahydro-2-benzazepine.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 74 (1), 18-30, 2016
公益社団法人 有機合成化学協会
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詳細情報
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- CRID
- 1390001205340731648
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- NII論文ID
- 130005126248
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 027053139
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可