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 (https://doi.org/10.1002/ejoc.200800672)
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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.
ORCID iDs
Porzelle, Achim, Woodrow, Michael D. and Tomkinson, Nicholas C. O. ORCID: https://orcid.org/0000-0002-5509-0133;-
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Item type: Article ID code: 34169 Dates: DateEvent2008PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 20 Oct 2011 13:40 Last modified: 28 Sep 2024 07:29 URI: https://strathprints.strath.ac.uk/id/eprint/34169