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Synthesis 1988; 1988(10): 807-808
DOI: 10.1055/s-1988-27716
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Reinvestigation of a Novel N-N Bond Formation Between Activated Hydroxamic Acids and Primary Amines

Willy Hartmann*
  • *Zentralbereich Forschung und Entwicklung, Wissenschaftliches Hauptlaboratorium der Bayer AG, D-4150 Krefeld-Uerdingen, Federal Republic of Germany
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Publication Date:
12 September 2002 (online)

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A recently reported synthesis of 1-acyl-2-alkylhydrazines from hydroxamic acids and primary amines using p-toluenesulfonyl chloride or 2-chloro-1-methylpyridinium iodide as activating agents has been reinvestigated and found to be erroneous. Lossen rearrangement occurs prior to N-N bond formation. The resulting isocyanates combine with the amines to give ureas.