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N-Methylimidazole-catalyzed Synthesis of Carbamates from Hydroxamic Acids via the Lossen Rearrangement

Sabesan Yoganathan and Scott J. Miller*

*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States, Email:

S. Yoganathan, S. J. Miller, Org. Lett., 2013, 15, 602-605.

DOI: 10.1021/ol303424b

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A catalytic amount of N-methylimidazole (NMI) accelerated a mild one-pot synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers.

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Key Words

Lossen Rearrangement, Isocyanates, Carbamates

ID: J54-Y2013-0320