Rearrangement of differentially protected N-arylhydroxylamines

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

Research output: Contribution to journalArticle

19 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.
LanguageUndefined/Unknown
Pages5135-5143
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - 2008

Keywords

  • N-arylhydroxylamines
  • 2-aminophenols
  • organic chemistry

Cite this

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title = "Rearrangement of differentially protected N-arylhydroxylamines",
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.",
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author = "Achim Porzelle and Woodrow, {Michael D.} and Tomkinson, {Nicholas C. O.}",
year = "2008",
doi = "10.1002/ejoc.200800672",
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Rearrangement of differentially protected N-arylhydroxylamines. / Porzelle, Achim; Woodrow, Michael D.; Tomkinson, Nicholas C. O.

In: European Journal of Organic Chemistry, No. 30, 2008, p. 5135-5143.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Rearrangement of differentially protected N-arylhydroxylamines

AU - Porzelle, Achim

AU - Woodrow, Michael D.

AU - Tomkinson, Nicholas C. O.

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

KW - N-arylhydroxylamines

KW - 2-aminophenols

KW - organic chemistry

U2 - 10.1002/ejoc.200800672

DO - 10.1002/ejoc.200800672

M3 - Article

SP - 5135

EP - 5143

JO - European Journal of Organic Chemistry

T2 - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 30

ER -