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Wharton reaction

The Wharton reaction is the chemical reaction of α,β-epoxy-ketones with hydrazine to give allylic alcohols.[1][2][3]

Dupuy has developed an improved procedure.[4]

Reaction mechanism

The mechanism of the Wharton reaction begins with reaction of the ketone (1) with hydrazine to form a hydrazone (2). Rearrangement of the hydrazone gives intermediate 3, which can decompose giving off nitrogen gas forming the desired product 4. Stork et al. have investigated the mechanism of the final decomposition and found that it can proceed by an ionic mechanism or a radical mechanism depending on reaction temperature, solvent used, and structure of intermediate 3.[5]

Notice that the alcohol retains the configuration of the starting epoxide.


  1. ^  Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615.
  2. ^  Wharton, P. S. J. Org. Chem. 1961, 26, 4781.
  3. ^  Chamberlin, A. R.; Sall, D. J. Comp. Org. Syn. 1991, 8, 927-929. (Review)
  4. ^  Dupuy, C.; Luche, J. L. Tetrahedron 1989, 45, 3437.
  5. ^  Stork, G. A. et al. J. Am. Chem. Soc. 1977, 99, 7067.

See also

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Wharton_reaction". A list of authors is available in Wikipedia.
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