N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

Lev M. Yagupolskii, Irina I. Maletina, Liubov V. Sokolenko, Yurii G. Vlasenko, Sergey A. Buth

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The analogues of carboxamides in which the sp2-hybridized oxygen atom is replaced by more electron-withdrawing groups, {double bond, long}NSO2CF3 and {double bond, long}NSO2C4F9, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC({double bond, long}NSO2Rf)NH2 (Rf = CF3, C4F9) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN{double bond, long}C{double bond, long}NSO2Rf under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC({double bond, long}NSO2R)NH2 (R = CH3, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R.

Original languageEnglish (US)
Pages (from-to)486-492
Number of pages7
JournalJournal of Fluorine Chemistry
Volume129
Issue number6
DOIs
StatePublished - Jun 1 2008

Keywords

  • Amidines
  • Carbodiimides
  • Rearrangements
  • X-ray structure

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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