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Rearrangement of Differentially Protected N ‐Arylhydroxylamines
Author(s) -
Porzelle Achim,
Woodrow Michael D.,
Tomkinson Nicholas C. O.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800672
Subject(s) - chemistry , aniline , yield (engineering) , aryl , phenol , medicinal chemistry , stereochemistry , organic chemistry , alkyl , materials science , metallurgy
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, 69451 Weinheim, Germany, 2008)