Direct observation of dienol intermediates in photochemical deconjugation of an .ALPHA.,.BETA.-uusaturated ketone. Photoisomerization of 1-acetylcyclooctene.
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概要
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The photolysis of 1-acetylcyclooctene in acetonitrile solution leads to 3-(α-hydroxyethylidene)cyclooctene (two stereoisomers). Structures of the stable 1,3-dienols have been elucidated on the basis of their spectral data and chemical behavior. The dienols are highly air-sensitive. Upon heating, or by the action of an acid or base, they are converted to 3-acetylcyclooctene. In methanol-<I>O</I>-<I>d</I>, 3-acetylcyclooctene-3-<I>d</I> is formed. These findings provide the first, unambiguous evidence for the intervention of 1,3-dienol intermediates in photochemical deconjugation of an α,β-unsaturated ketone into the β,γ isomer.
- 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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KATO Masao
Department of Agricultural Chemistry, The University of Tokyo
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NOYORI Ryoji
Department of Chemistry, Nagoya University
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Inoue Hiroshi
Deparment of Neurosurgery, Gunma University School of Medicine and Gamma Unit Center, Hidaka Hospital
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