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Synthesis 1988; 1988(7): 547-549
DOI: 10.1055/s-1988-27634
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A Convenient Synthesis of Sterically Hindered Geminal Dibromides

Frank S. Guziec, Jr.* , Lynn James Sanfilippo
  • *Department of Chemistry, New Mexico State University, Las Cruces, NM 88003, USA
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Publication Date:
18 September 2002 (online)

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The treatment of sterically hindered hydrazones with two equivalents of bromine and an excess of triethylamine in ether afforded sterically hindered geminal dibromides in good yields. The diazo compound appears to be an intermediate in this reaction. Direct treatment of the corresponding diazo compounds with one equivalent of bromine in ether also afforded the geminal dibromides. A comparison of these methods indicated that aliphatic dibromides were best prepared directly from the hydrazones, while diaryl derivatives were best prepared using isolated diazo compounds.

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