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Hiroshi Takeuchi, Toshikazu Nagai, Niichiro Tokura, The Effect of Sulfur Dioxide in the Radical Reactions of Anthracene, Bulletin of the Chemical Society of Japan, Volume 40, Issue 10, October 1967, Pages 2375–2379, https://doi.org/10.1246/bcsj.40.2375
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Abstract
The reaction of anthracene with benzoyl peroxide (BPO) in benzene solution gives 9-benzoyloxyanthracene (I), without forming any 9,10-dibenzoyloxyanthracene (II). However, in the presence of sulfur dioxide (SO2), the above mentioned reaction produces II, 9,9′-dianthrone (III), and anthraquinone (IV), without any I. These reaction mechanisms could be interpreted as follows: It is considered that, in the addition reaction of anthracene with a benzoyloxy radical (PhCOO·), the 9,10-dihydro-9-benzoyloxyanthryl radical (V) is formed. In the absence of SO2, an intra-molecular aromatization of V occurs by a hydrogen abstraction and a delocalization of the radical. On the contrary, in the presence of SO2, the localization of the V radical is enhanced by the interaction with SO2, thus promoting the reactivity toward the benzoyloxy radical. Moreover, in the experiments using α, α′-azobis-isobutyronitrile (AIBN) in place of BPO, the addition products of 2-cyano-2-propyl radicals with anthracene were isolated. This phenomenon could be explained by the fact that the hydrogen abstractions of the addition products do not occur.
