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

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

doi:10.1055/s-0028-1087943

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

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

24 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%).

Original language	Undefined/Unknown
Pages (from-to)	798-802
Number of pages	5
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-0028-1087943
Publication status	Published - 2009

Keywords

hydroxy carbamates
N-aryl-N-hydroxy carbamates
chloroformates

Access to Document

10.1055/s-0028-1087943

Cite this

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title = "Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates",

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\%). ",

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year = "2009",

doi = "10.1055/s-0028-1087943",

language = "Undefined/Unknown",

pages = "798--802",

journal = "Synlett",

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T1 - Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates

AU - Porzelle, Achim

AU - Woodrow, Michael D.

AU - Tomkinson, Nicholas C. O.

PY - 2009

Y1 - 2009

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

M3 - Article

SN - 0936-5214

SP - 798

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JO - Synlett

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