Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 2087-2091Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300007c
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Funding
- National Science Foundation [CHE-1009038]
- Direct For Mathematical & Physical Scien [1009038] Funding Source: National Science Foundation
- Division Of Chemistry [1009038] Funding Source: National Science Foundation
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A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-lambda(3)-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. 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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