The reaction of anthracene with sulfur dioxide in the presence of benzoyl peroxide : The formation of anthracene sulfones

Abstract

The reaction of anthracene with SO 2 in the presence of benzoyl peroxide using n-heptane as solvent, yielded anthronyl phenyl sulfone, oligomers ( anthracene polysulfones), diphenyl disulfone, benzenesulfonic acid, anthraquinone, benzoic acid and benzene. If benzene was used as solvent, the formation of the sulfones mentioned above was not observed, and instead the reaction yielded 9,10-dibenzoyloxyanthracene, dianthrone, anthraquinone, benzoic acid and a trace of benzene-sulfonic acid. These results have been interpreted in terms of a C-T complex 1 of anthracene-sulfur dioxide, since the sulfones are readily formed in a solvent such as n-heptane which does not interact with SO 2, whereas the formation of the sulfones is diminished in a solvent such as benzene due to its interaction with SO 2. 2 As in the reaction of SO 2 with benzoyl peroxide using n-heptane as a solvent, diphenyl disulfone, benzenesulfonic acid, benzoic acid, benzene, phenyl benzoate and diphenyl disulfide were isolated; the yields of diphenyl disulfone, benzenesulfonic acid and diphenyl disulfide being derived from the phenylsulfonyl radical were larger than those obtained from the reaction with anthracene, the phenyl radical readily reacts with SO 2 in the absence of anthracene, but the formation of the phenylsulfonyl radical is diminished in the presence of anthracene. And these results might be interpreted in terms of the interaction of anthracene with SO 2 rather than with the phenyl radical, because phenylanthracene derivatives did not form but some anthracene sulfone was obtained.