HYDROXYKETONES. PART VI. THE FRIES REARRANGEMENT OF THE PHENOLIC ESTERS OF o- AND m-NITROBENZOIC ACIDS AND SOME THIOPHENYL ESTERS

The Fries migrations of o- and m-nitrohenzoic acid esters with phenol, isomeric cresols and naphthols have been studied. The esters of m-nitrobenzoic acid afforded normal migration products while the reaction failed with the esters of o-nitrobenzoic acid. This behaviour could be explained due to the absence of complex formation at the phenoxyl oxygen, which is sterically hindered. The migrations of thiophenyl acetate and benzoate were also tried, but without any success