Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: Reaction scope and limitations

Aleksandra A. Zagulyaeva, Christopher T. Banek, Mekhman S. Yusubov, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)4644-4647
Number of pages4
JournalOrganic Letters
Volume12
Issue number20
DOIs
StatePublished - Oct 15 2010
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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