PHOTOREACTIONS VIA π-π* AND n-π* TRIPLET STATES OF FLAVANONES

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Abstract
Photolyses of flavanone and substituted flavanones in benzene led to the cleavage of the pyrone ring to give corresponding 2′-hydroxychalcones, while similar irradiation of flavanone or 4-chromanone in 2-propanol gave coupling products (pinacols and solvent adducts). However, photolysis of 7,8-benzoflavanone in 2-propanol led to the cleavage of the pyrone ring instead of the formation of coupling products. It is implied that the cleavage of the pyrone ring takes place via π-π* triplet states, while formation of coupling products via n-π* triplet states.

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