Rearrangement of differentially protected N-arylhydroxylamines

Achim Porzelle, Michael D. Woodrow, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

21 Citations (Scopus)

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 languageUndefined/Unknown
Pages (from-to)5135-5143
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - 2008

Keywords

  • N-arylhydroxylamines
  • 2-aminophenols
  • organic chemistry

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