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Photochemistry of Substituted 4,4‐Dimethoxy‐2,5‐Cyclohexadienones
Author(s) -
Hong FangTsao,
Lee KungShing,
Tsai YowFu,
Liao ChunChen
Publication year - 1998
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199800001
Subject(s) - chemistry , hydroquinone , methanol , benzene , phenol , irradiation , thallium , phenols , photochemistry , organic chemistry , medicinal chemistry , nuclear physics , physics
4,4‐Dimethoxy‐2,5‐cyclohexadienones 9–14 were prepared from the corresponding hydroquinone monomethyl ethers by oxidation with thallium trinitrate in methanol. Irradiation of solutions of 9–13 in methanol with a broad band of UV light centered at 350 nm in a Rayonet reactor afforded 2‐cyclopentenone derivatives 15–19 in moderate to excellent yields, whereas irradiation of 14 in methanol gave phenol 8 along with other unidentified products. Irradiation of 11–14 in benzene yielded substituted phenols. The plausible reaction pathways for the product formation are discussed.