New Photochemical Reactions of 9-ω-Bromoacetylanthracene. I

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New photochemical reactions were found on 9-ω-bromoacetylanthracene. The main photo-products were 1-aceanthrenone and 9-bromoanthracene. Their formation was not appreciably affected by the presence of oxygen. Other products such as anthracene, 9-acetylanthracene and anthraquinone were also detected and their yields greatly depended on the reaction conditions. From the low temperature experiments, it was made clear that 9-bromoanthracene and 1-aceanthrenone were formed <I>via</I> different mechanisms. A rather stable intermediate, which was not a radical but presumably an intramolecular adduct, was detected spectroscopically. 1-Aceanthrenone was formed from the intermediate both photochemically and thermally with liberation of hydrogen bromide. In the absence of oxygen both the thermal and photochemical reactions of the intermediate yielded almost the same amount of 1-aceanthrenone. The reaction mechanisms were considered in reference to the photochemical reactions of 9-nitroanthracene and sodium 9-anthroate. The relation between these reactions and the radiationless transition processes of carbonyl derivatives of anthracene was also discussed.
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