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Korean Society of Photoscience (한국광과학회)
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Photoaddition Reactions of 1,2-Diketone

  • Park, Hea Jung (Department of Chemistry and Chemical Institute for Functional Materials, Pusan National University) ;
  • Seo, Jung Soo (Department of Chemistry and Chemical Institute for Functional Materials, Pusan National University) ;
  • Yoon, Ung Chan (Department of Chemistry and Chemical Institute for Functional Materials, Pusan National University) ;
  • Cho, Dae Won (Department of Chemistry, Yeungnam University)
  • Received : 2012.02.01
  • Accepted : 2012.02.21
  • Published : 2012.03.01
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Abstract

Photoaddition reactions between 1,2-dicarbonyl compounds and silyl enol ethers in acetonitrile and benzene were explored. Irradiation of acetonitrile or benzene solutions containing 1,2-diketone, acenaphthalquinone, phenanthrene-quinone and silyl enol ethers is observed to promote the production of 1,4-dioxenes, oxetanes, and ${\beta}$-hydroxyketone by the [4+2]-cycloadditon, Paterno-Buchi processes, and SET promoted Claisen-type condensation. Among these competitive pathways leading to the generation of each types of products, SET promoted 1,4-dioxene and ${\beta}$-hydroxyketone formation are more favored regardless of solvent polarity.

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References

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