Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Singlet-Triplet Reactivity of 1-Methyl-2-Cyclohexenyl Aryl Ketones : Racemization vs 1,3-Acyl Shift in the Excited States

  • Woo Ki Chae (Department of Chemistry Education, Seoul National University) ;
  • Mi Young Chae (Department of Chemistry Education, Seoul National University) ;
  • Mi Kyung Park (Department of Chemistry Education, Seoul National University) ;
  • Chung Hee Lee (Department of Chemistry Education, Seoul National University) ;
  • Eun Hee You (Department of Chemistry Education, Seoul National University)
  • Published : 1990.06.20
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Abstract

The photochemistry of 1-Methyl-2-cyclohexenyl aryl ketones (phenyl ketone 7a, p-toluyl ketone 7b, biphenyl ketone 7c and -naphthyl ketone 7d) is reported. The aryl ketone 7a, 7b and 7c undergo photo-racemization with efficiencies of 0.75, 0.79 and 0.76 respectively on direct irradiation. Direct irradiation of the ketone 7d, however, undergoes 1,3-shift with an efficiency of 0.02. Triplet states are responsible for the racemizations and singlet state is responsible for 1,3-shift as in general. The ketone 7a, 7b and 7c are good example of a few ${\beta},{\gamma}$-unsaturated ketones which undergo efficient intersystem crossing on direct irradiation.

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