The Baeyer-Villiger oxidation of 8-oxabicyclo(3.2.1)octan-3-ones. Substituent effects on the regioselectivity.
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概要
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8-Oxabicyclo[3.2.1]octan-3-one derivatives serve as excellent models that elucidate factors controlling the reactivities and selectivities in the Baeyer-Villiger oxidation. The regioselectivity of the oxidation with trifluoroperacetic acid is markedly affected by the electronic properties of substituents at position α or β to the carbonyl function. Remote effects of the γ-substituents are also of significance. This study has disclosed yet unrecognized through-bond electronic influence and regioselection based on chiral orientation of hydroxyl group in the transient tetrahedral intermediate.
- 公益社団法人 日本化学会の論文
著者
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Noyori Ryoji
Department Of Chemistry And Molecular Chirality Research Unit Nagoya University
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Sato Tsuneo
Department Of Life Science Kurashiki University Of Science And The Arts
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Kobayashi Hiroshi
Department Of Applied Physics School Of Science And Engineering Waseda University
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Sato Tsuneo
Department of Chemistry, Nagoya University
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