N,N‘-Ditosylhydrazine:  A Convenient Reagent for Facile Synthesis of Diazoacetates†

  • 10.1021/ol701432k
  • Organic Letters
  • p 3195-3197, Volume 9, Issue 16,
  • journal-article
A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N‘-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.


Reproducible, but Yields Lower Than Described


An efficient method for the synthesis of diazoacetates from the coresponding bromoacetates and N,N'-ditosylhydrazine has been described. In fact, diazoacetates can be prepared from various alcohols by acylation with bromoacetyl bromide, followed by a treatment with...