Abstract
The rearrangement of a series of N,O-difunctionalized N-arylhydroxylamines to generate protected 2-aminophenols has been investigated. N-Boc-N-aryl-O-acylhydroxylamines are stable, isolable compds. which rearrange smoothly at temps. between 110 and 140°C. The corresponding N-Boc-N-aryl-O-sulfonylhydroxylamines were not isolated and rearrange to 1,2-difunctionalized aminophenols at room temp. in excellent yield. Deprotection of either the N- or O-substituents under std. conditions allows for further synthetic manipulation of either the aniline or phenol functionality.
Original language | Undefined/Unknown |
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Pages (from-to) | 5135-5143 |
Number of pages | 9 |
Journal | European Journal of Organic Chemistry |
Issue number | 30 |
DOIs | |
Publication status | Published - 2008 |
Keywords
- N-arylhydroxylamines
- 2-aminophenols
- organic chemistry