(Tosylimino)phenyl-λ3-iodane as a Reagent for the Synthesis of Methyl Carbamates via Hofmann Rearrangement of Aromatic and Aliphatic Carboxamides
Akira Yoshimura, Matthew W. Luedtke and Viktor V. Zhdankin*
*Department of Chemistry and Biochemistry, University of Minnesota-Duluth, Duluth, Minnesota 55812, United States, Email: vzhdankid.umn.edu
A. Yoshimura, M. W. Luedtke, V. V. Zhdankin, J. Org. Chem., 2012, 77, 2087-2091.
DOI: 10.1021/jo300007c (free Supporting Information)
The use of PhINTs as a reagent enables a mild Hofmann rearrangement of aromatic and aliphatic carboxamides. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.
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A. A. Zagulyaeva, C. T. Banek, M. S. Yusubov, V. V. Zhdankin, Org. Lett., 2010, 12, 4644-4647.