Photoreactions of Flavanones

Parent and substituted flavanones undergo photochemical opening of the pyrone ring to give corresponding 2′-hydroxychalcones in benzene, pyridine, acetonitrile etc., the yields varying from 0 to 70% with substituents. The reaction is depressed by the addition of 1,3-pentadiene, nitrosobenzene, or ac...

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Published inBulletin of the Chemical Society of Japan Vol. 53; no. 10; pp. 2938 - 2942
Main Authors Matsushima, Ryoka, Kishimoto, Tsuneo, Suzuki, Morio, Morioka, Motonobu, Mizuno, Hideo
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.01.1980
Chemical Society of Japan
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Summary:Parent and substituted flavanones undergo photochemical opening of the pyrone ring to give corresponding 2′-hydroxychalcones in benzene, pyridine, acetonitrile etc., the yields varying from 0 to 70% with substituents. The reaction is depressed by the addition of 1,3-pentadiene, nitrosobenzene, or acrylonitrile. On the other hand, flavanone and 4-chromanone undergo photoreduction in 2-propanol to give reductive coupling products and solvent adducts as isomeric mixtures. 7,8-Benzoflavanone does not undergo photoreduction in 2-propanol but the ring opening reaction instead. Mechanisms have been discussed in terms of the relative contribution and π,π* character in the lowest triplet states.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.53.2938