Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An efficient 1-pot procedure for the Zn-mediated redn. of nitro arenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixts. in good to excellent yield (34-81%). Solvolysis of the bisprotected hydroxylamines with NaOMe at room temp. provides access to synthetically versatile N-aryl-N-hydroxy carbamates in excellent yields (89-97%).
LanguageUndefined/Unknown
Pages798-802
Number of pages5
JournalSynlett
Issue number5
DOIs
Publication statusPublished - 2009

Keywords

  • hydroxy carbamates
  • N-aryl-N-hydroxy carbamates
  • chloroformates

Cite this

Porzelle, Achim ; Woodrow, Michael D. ; Tomkinson, Nicholas C. O. / Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates. In: Synlett. 2009 ; No. 5. pp. 798-802.
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Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates. / Porzelle, Achim; Woodrow, Michael D.; Tomkinson, Nicholas C. O.

In: Synlett, No. 5, 2009, p. 798-802.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Woodrow, Michael D.

AU - Tomkinson, Nicholas C. O.

PY - 2009

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N2 - An efficient 1-pot procedure for the Zn-mediated redn. of nitro arenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixts. in good to excellent yield (34-81%). Solvolysis of the bisprotected hydroxylamines with NaOMe at room temp. provides access to synthetically versatile N-aryl-N-hydroxy carbamates in excellent yields (89-97%).

AB - An efficient 1-pot procedure for the Zn-mediated redn. of nitro arenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixts. in good to excellent yield (34-81%). Solvolysis of the bisprotected hydroxylamines with NaOMe at room temp. provides access to synthetically versatile N-aryl-N-hydroxy carbamates in excellent yields (89-97%).

KW - hydroxy carbamates

KW - N-aryl-N-hydroxy carbamates

KW - chloroformates

U2 - 10.1055/s-0028-1087943

DO - 10.1055/s-0028-1087943

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T2 - Synlett

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