Abstract
Photochemical studies on 1,4-bis(phenylsulfonyloxy)benzene were performed in acetonitrile by steady-state photolysis at 254 nm. Analysis of photoproducts demonstrate that 1,4-bis(phenylsulfonyloxy)benzene undergoes S–O cleavage leading to the formation of phenylsulfonyl radical and phenylsulfonyloxyphenoxy radical which result in the formation of Fries rearrangement products or escape from the solvent cage to undergo further transformations. The involvement of triplet state in the photo-Fries rearrangement was detected. During the irradiation process, a large amount of acidic species were observed and the formation of benzenesulfonic acid was confirmed. Involvement of O2 in the acid generation was proved to be a primary pathway by comparative experiments. Another pathway of acid generation could be explained as a result of disproportionation of sulfonyl radicals due to the formation of thiobenzenesulfonate. The quantification of the acid was determined by the acid–base titration and investigation on steady-state photolysis was carried out by HPLC analysis and GC–MS.
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