Conversion of aliphatic amides into amines with [I, I-bis (trifluoroacetoxy) iodo] benzene. 1. Scope of the reaction

GM Loudon, AS Radhakrishna…

文献索引：Loudon, G. Marc; Radhakrishna, A. S.; Almond, Merrick R.; Blodgett, James K.; Boutin, Raymond H. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4272 - 4276

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被引用次数: 150

摘要

The reagent [IJ-bis (trifluoroacetoxy) iodo] benzene, PIFA, brings about the facile oxidative rearrangement of aliphatic amides to amines in mildly acidic (pH 1-3) mixed aqueous- organic solvents. Aromatic amines are further oxidized by the reagent and therefore cannot be prepared by this method. The rearrangement, which is in effect an" acidic Hofmann rearrangement", occurs with complete retention of configuration in the migrating group, ...