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)

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.

ORCID iDs

Tomkinson, Nicholas C. O. ORCID: https://orcid.org/0000-0002-5509-0133

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• Item metadata

  Item type:	Article
  ID code:	34169
  Dates:	Date Event 2008 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	20 Oct 2011 13:40
  Last modified:	11 Nov 2024 09:52
  URI:	https://strathprints.strath.ac.uk/id/eprint/34169