959085-01-9Relevant academic research and scientific papers
Rearrangement of differentially protected N-arylhydroxylamines
Porzelle, Achim,Woodrow, Michael D.,Tomkinson, Nicholas C. O.
experimental part, p. 5135 - 5143 (2009/06/17)
The rearrangement of a series of N,O-difunctionalised N-arylhydroxylamines to generate protected 2-aminophenols has been investigated. N-Boc-N-Aryl-O- acylhydroxylamines are stable, isolable compounds which rearrange smoothly at temperatures between 110 and 140°C. The corresponding N-Boc-N-aryl-O- sulfonylhydroxylamines were not isolated and rearrange to 1,2-difunctionalised aminophenols at room temperature in excellent yield. Deprotection of either the N- or O-substituents under standard conditions allows for further synthetic manipulation of either the aniline or phenol functionality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
