Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

Samuel Braverman, Marina Cherkinsky, Ludmila Kedrova

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The preparation of several N-monosubstituted trichlorothioacetamides by thionation of the corresponding acetamides, with the use of Heimgartner's reagent is described. In contrast to the corresponding amides which undergo base-induced β-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)9259-9262
Number of pages4
JournalTetrahedron Letters
Issue number50
StatePublished - 10 Dec 1998

Bibliographical note

Funding Information:
Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.


  • Amides
  • Favorskii rearrangement
  • Thioamides


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