Science of Synthesis

Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1654.

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 C—O bond but a C—F bond.[‌402‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 8888.
• 8.Meeeee-Meee, (8888) 8/8e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 8888.