Phenyl formate, deacylation

The H202-HF-SbF5 system has been applied by Jacquesy and co-workers in the hydroxylation of a variety of functionalized arenes.624 Hydroxylation of phenyl esters has been shown to afford themeta and para isomers as main products625 [Eq. (5.217)]. Substantial amounts of the deacylated derivatives were obtained in the reaction of phenyl formate and diphenyl carbonate. In the hydroxylation of 2-chlorophenyl and 4-chlorophenyl acetate, regioselectivity is controlled by the chlorine substituent with the hydroxyl entering into the meta position to the ester group.626 A similar effect was observed in the hydroxylation of anilines and anilides. 

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