書誌事項
- タイトル別名
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- Chemistry of Benzocyclobutenols.
- ベンゾシクロブテノール ノ カガク
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Photochemical cyclization of substituted o-alkylphenyl ketones and the thermal and acid-catalyzed reactions of the resulting benzocyclobutenols are described. The selective thermal ring opening of the benzocyclobutenol to the E-dienol was elucidated using the deuterated benzocyclobutenol and by thermal interconversion between two diastereomeric benzocyclobutenols. The 2, 2-dimethylbenzocyclobutenols having a hydroxy group on the β-carbon of the quaternary C1-alkyl group underwent stereospecific thermal isomerization by a 1, 5-sigmatropic hydrogen shift to give the 2-isopropenylphenyl alcohol through a twisted E-dienol. The benzocyclobutenols having a keto group on the β-carbon of the quaternary C1-alkyl group underwent thermal retro-aldol cleavage to give benzocyclobutenones. Acid-catalyzed reaction of benzocyclobutenols having α, α-dimethyl and β-hydroxy or β-acetoxy groups in their C1-alkyl chain gave isopropylidenebenzocyclobutene.
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 59 (7), 689-696, 2001
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205276473728
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- NII論文ID
- 10012288117
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 5834738
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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
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- 抄録ライセンスフラグ
- 使用不可