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Synlett 2000; 2000(11): 1673-1675
DOI: 10.1055/s-2000-7938
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A "One-Pot" Procedure for the Oxidative Conversion of Alkyl Halides and Tosylates to N,N-Dimethylhydrazones

Ian C. Barrett* , Michael A. Kerr
  • *Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada; E-mail: makerr@julian.uwo.ca
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Publication History

Publication Date:
31 December 2000 (online)

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The treatment of a solution of an alkyl halide with sodium azide results in the formation of a solution of the alkyl azide, which upon filtration to remove the sodium halide, is treated with N,N-dimethyl hydrazine and catalytic FeCl3 · 6H2O under refluxing conditions. The result is a one pot conversion of an alkyl halide to an N,N-dimethyl hydrazone, a net oxidation of the halogen-bearing carbon.

hydrazones - iron - azides - alkyl halides - catalysis

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