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.
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Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.
- Favorskii rearrangement