Photoreaction of Acetoacetate

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概要

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• Methyl acetoacetate was irradiated in the presence of cyclohexene to afford methyl 3-cyclohexyl-3-hydroxybutyrate (VIII), methyl 3-cyclohexenyl-3-hydroxybutyrate (IX), two oxetanes (Xa and Xb), and cyclohexene dimers. In contrast to acetylacetone, acetoacetate behaves as a saturated ketone rather than as an α,β-unsaturated ester on photoreaction. We concluded that the <I>n</I>-π<SUP>*</SUP> excitation of the enol-form of β-dicarbonyl compound is responsible for photo-cycloaddition, and no effective <I>n</I>–π<SUP>*</SUP> excitation is accesisble on irradiaron of the enol-form of acetoacetate, since the enol form of acetoacetate has its <I>n</I>–π<SUP>*</SUP> and π-π<SUP>*</SUP> absorptions in the same region.

• 公益社団法人 日本化学会の論文

著者

• Sato Tadashi

  School of Science and Engineering, Waseda University

• Tada Masaru

  School of Science and Engineering, Waseda University

• Kokubo Tadayoshi

  School of Science and Engineering, Waseda University

関連論文

• Photoreaction of Acetoacetate
• The Ring-size Effect in the Photoreaction of Phenylcycloalkenes

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