Photochemical reactions of methyl 3-(o-alkylphenyl)-2,2-dimethyl-3-oxopropanoates in hexane gave
only the corresponding benzocyclobutenols. However, when irradiation was carried out in methanol,
3-oxonaphthalenones were produced together with the benzocyclobutenols. The ratio of benzocyclobutenol to naphthalenone depends on the bulkiness of the alkyl group in the ortho position.
Intermediary 1,4-diradicals or dienols were efficiently trapped by oxygen to afford the corresponding
peroxides and/or oxygenated compounds derived from the peroxides.
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