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Org Lett. 2013 Feb 1;15(3):602-5. doi: 10.1021/ol303424b. Epub 2013 Jan 17.

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

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  • 1Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.

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.

PMID:
23327543
[PubMed - indexed for MEDLINE]
PMCID:
PMC3563000
Free PMC Article
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