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 Vladimirovich Zhdankin

Research output: Contribution to journalArticle

51 Citations (Scopus)

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
Pages (from-to)4644-4647
Number of pages4
JournalOrganic Letters
Volume12
Issue number20
DOIs
Publication statusPublished - 15 Oct 2010

Fingerprint

Iodine
iodine
acetonitrile
quinones
Benzamides
amines
methyl alcohol
Oxidants
preparation
Amines
Methanol
Derivatives
potassium peroxymonosulfuric acid
iodobenzene
benzoquinone

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone : Reaction scope and limitations. / Zagulyaeva, Aleksandra A.; Banek, Christopher T.; Yusubov, Mekhman S.; Zhdankin, Viktor Vladimirovich.

In: Organic Letters, Vol. 12, No. 20, 15.10.2010, p. 4644-4647.

Research output: Contribution to journalArticle

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