The Wharton synthesis allows α,β-epoxyketones to be transformed into allylic alcohols by treatment with hydrazine in acetic acid medium or hydrazine hydrate followed by strong base. The \alpha,\beta-epoxyketone is obtained from the \alpha,\beta-unsaturated ketone by oxidation with hydrogen peroxide in a basic medium.

wharton synthesis 01

Starting from α-substituted ketones (haloketones, hydroxyketones, aminoketones), olefins are obtained by treatment with hydrazine in a basic medium under heating.

wharton synthesis 02

The mechanism of the Wharton rearrangement is very similar to that of the Wolff-Kishner reaction. It begins with protonation of the carbonyl, followed by attack by hydrazine to form a hydrazone, which on deprotonation releases nitrogen with formation of a vinyl anion. Protonation of the vinyl anion yields the final product.
wharton synthesis 03