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Photochemical Reduction of 2-Bromo-4,4-dimethyl-2-cyclohexenone

✍ Scribed by Hermann Hombrecher; Paul Margaretha

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
234 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The photochemical behaviour of 2‐Bromo‐4,4‐dimethyl‐2‐cyclohexenone (1) was studied in 2‐propanol and cyclohexane. In both solvents (n‐π*)‐excitation followed by intersystem crossing leads to population of a low‐lying triplet (T~1~) state, which can be quenched by 1,3‐cyclohexadiene but does not undergo chemical transformation efficiently. (π‐π*)‐Excitation affords 4,4‐dimethyl‐2‐cyclohexenone (2) as the only product. While in 2‐propanol 2 is formed in 60% from the S~2~‐state and in 40% from the T~2~‐state, in cyclohexane reduction occurs exclusively from this upper triplet state. The T~2~‐state can also be populated via energy transfer using acetone or benzene as sensitizer. The mechanistic dissimilarities for the reduction of excited 1 in either 2‐propanol or cyclohexane are discussed.

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