title: Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: reaction scope and limitations.
abstract: Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in aqueous acetonitrile. On the basis of this reaction, a convenient experimental procedure for the preparation of alkylcarbamates using Oxone as the oxidant in the presence of iodobenzene in methanol has been developed. An efficient method for direct conversion of substituted benzamides to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile has also been found.
authors.affiliation: Department of Chemistry and Biochemistry, University of Minnesota, Duluth, Minnesota 55812, USA.
authors.forename: Aleksandra A
authors.initials: AA
authors.lastname: Zagulyaeva
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Banek
authors.forename: Mekhman S
authors.initials: MS
authors.lastname: Yusubov
authors.forename: Viktor V
authors.initials: VV
authors.lastname: Zhdankin
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013464:Sulfuric Acids / Q000737:chemistry*
chemical_list: D000081:Acetamides; D007462:Iodobenzenes; D013464:Sulfuric Acids; D007455:Iodine; C031905:iodobenzene; C048813:potassium peroxymonosulfuric acid