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• W2006585441 abstract "Ultraviolet irradiation of (+)-isopiperitenone (4) and (±)-4-acetoxyisopiperitenone (26) in cyclohexane using a Pyrex filter afforded (+)-1,2-dimethyltricyclo[3.3.0.02,7]octan-6-one (5) in 35–42% yield and 5-acetoxy-1,2-dimethyltricyclo[3.3.0.02,7]octan-6-one (28) in 42% yield, respectively. Irradiation of (+)-4 in methanol produced (+)-ketone 5 in 25% yield and (±)-5-carbomethoxymethyl-1,5-dimethylcyclohexene (6) in 49% yield. In methanol (±)-26 was photochemically converted to 28 (15%) and 4-carbomethoxymethyl-1-acetoxy-2,4-dimethylcyclohexene (29) (65%). Hydrolysis of 28 yielded the alcohol derivative 30. Treatment of 5 and 30 with hydrogen bromide produced the bromoketones 10 and 31, respectively. A mechanism for production of the esters 6 and 28 is presented which involves an unprecedented cleavage of an α,β-unsaturated ketone." @default.
• W2006585441 created "2016-06-24" @default.
• W2006585441 creator A5075969476 @default.
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• W2006585441 date "1969-01-01" @default.
• W2006585441 modified "2023-10-09" @default.
• W2006585441 title "Photochemistry of isopiperitenone and 4-acetoxyisopiperitenone. An unprecedented photochemical reaction of an α,β-unsaturated ketone" @default.
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• W2006585441 doi "https://doi.org/10.1016/s0040-4020(01)82796-4" @default.
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