title: N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement.
abstract: 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.
authors: Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.
authors: Sabesan
authors: S
authors: Yoganathan
authors: Scott J
authors: SJ
authors: Miller
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006877:Hydroxamic Acids / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers
chemical_list: D002219:Carbamates; D002712:Chlorides; D004952:Esters; D006877:Hydroxamic Acids; D007093:Imidazoles; D011108:Polymers; C018100:1-methylimidazole