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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 11, Number 3
BKCSDE 11(3)
March 20, 1990 

Singlet-Triplet Reactivity of 1-Methyl-2-Cyclohexenyl Aryl Ketones : Racemization vs 1,3-Acyl Shift in the Excited States
Woo Ki Chae*, Mi Young Chae, Mi Kyung Park, Chung Hee Lee, Eun Hee You
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 β,γ-unsaturated ketones which undergo efficient intersystem crossing on direct irradiation.
241 - 244
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