The Wharton reaction is the chemical reaction
to give allylic alcohols
Dupuy has developed an improved procedure.
The mechanism of the Wharton reaction begins with reaction of the ketone (1
) with hydrazine to form a hydrazone
). 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
Notice that the alcohol retains the configuration of the starting epoxide.The reaction is named after Peter Stanley Wharton.
- Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615.
- Wharton, P. S. J. Org. Chem. 1961, 26, 4781.
- Chamberlin, A. R.; Sall, D. J. Comp. Org. Syn. 1991, 8, 927-929. (Review)
- Dupuy, C.; Luche, J. L. Tetrahedron 1989, 45, 3437.
- Stork, G. A. et al. J. Am. Chem. Soc. 1977, 99, 7067.