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: tomkinsonnccardiff.ac.uk
A. Porzelle, M. D. Woodrow, N. C. O. Tomkinson, Synlett, 2009, 798-802.
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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reduction of nitro compounds, hydroxylamines, carbamates, zinc-mediated reduction, cleavage of carbonates