Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemistry of 2-Methoxy-2, 5-cyclohexadienone. IV. Photochemistry of 2-Methoxy-4, 4-diphenyl-2, 5-cyclohexadienone and 4-Dichloromethyl-2-methoxy-4-methyl-2, 5-cyclohexadienone
KATSUHIDE MATOBAFUJIKO KAWAGOSHIMINAKO TANABETAKAO YAMAZAKI
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1985 Volume 33 Issue 9 Pages 3709-3714

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Abstract
2-Methoxy-4, 4-diphenyl-2, 5-cyclohexadienone (Ib) was irradiated with a 100 W mercury lamp in methanol to give methyl 5-methoxy-6, 6-diphenyl-2, 5-hexadienoate (II) or its oxidized product, 9-(4-carbomethoxy-1-methoxy-2-butenylidene)-9H-fluorene (IV), and in benzene to give 6-methoxy-5, 6-diphenyl-2, 4-cyclohexadienone (VI) and 1-methoxy-6, 6-diphenylbicyclo [3.1.0] hex-3-en-2-one (VII). 2-Methoxy-4, 4-diphenyl-2-cyclohexenone (XIa) was irradiated in benzene or methanol to give 1-methoxy-5, 6-diphenylbicyclo [3.1.0] hexan-2-one (XII) in good yield. Finally, 4-dichloromethyl-2-methoxy-4-methyl-2, 5-cyclohexadienone (Ic) in methanol gave 6-dichloromethyl-2, 2-dimethoxy-6-methylbicyclo [3.1.0] hexan-3-one (XIV) and 5-dichloromethyl-6, 6-dimethoxy-5-methyl-2-cyclohexenone (XV).
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© The Pharmaceutical Society of Japan
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