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

AA Zagulyaeva, CT Banek, MS Yusubov…

Index: Zagulyaeva, Aleksandra A.; Banek, Christopher T.; Yusubov, Mekhman S.; Zhdankin, Viktor V. Organic Letters, 2010 , vol. 12, # 20 p. 4644 - 4647

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Citation Number: 46

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 ...