N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement.

Sabesan Yoganathan, Scott J Miller

Organic letters 2013 Feb 01

filter terms:

An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

Citation

Sabesan Yoganathan, Scott J Miller. N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement. Organic letters. 2013 Feb 01;15(3):602-5