Rearrangement of differentially protected N-arylhydroxylamines

Porzelle, Achim and Woodrow, Michael D. and Tomkinson, Nicholas C. O. (2008) Rearrangement of differentially protected N-arylhydroxylamines. European Journal of Organic Chemistry (30). pp. 5135-5143. ISSN 1434-193X

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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.