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Facile Procedure for the Synthesis of N-Aryl-N-hydroxy Carbamates

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

*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK, Email:

A. Porzelle, M. D. Woodrow, N. C. O. Tomkinson, Synlett, 2009, 798-802.

DOI: 10.1055/s-0028-1087943


An efficient one-pot procedure for the zinc-mediated reduction of nitroarenes in the presence of chloroformates leads to the corresponding N,O-bisprotected hydroxylamines in good yield under ambient conditions in THF-water mixtures. Solvolysis of the bisprotected hydroxylamines with sodium methoxide at room temperature provides access to synthetically versatile N-aryl-N-hydroxy carbamates in excellent yields.

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Key Words

reduction of nitro compounds, hydroxylamines, carbamates, zinc-mediated reduction, cleavage of carbonates

ID: J60-Y2009-0880