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Please login to access the full content or check if you have access via Variation 7: Replacement of an Aromatic C—H Bond by a C—O Bond

DOI: 10.1055/sos-SD-031-01728

Scholz, U.; Schlummer, B.Science of Synthesis, (2007311654.

When phenylhydroxylamine is heated in the presence of aqueous acids, e.g. sulfuric acid, the well-known Bamberger rearrangement[‌363‌] leads to the formation of 4-aminophenol (209) (Scheme 226).[‌361‌] Other arylhydroxylamines behave similarly. If the para position of the aryl group is substituted, the corresponding ortho products are formed. Variations of the Bamberger rearrangement exist; for example, when running the reaction at low temperature in the presence of hydrogen fluoride, the newly formed bond is not a CO bond but a CF bond.[‌402‌]

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