Wharton reaction

The general features of this synthesis are: 1) the epoxidation of α,β-unsaturated ketones is achieved usually in basic conditions using hydrogen peroxide solution in high yield; 2) the epoxy ketone is treated with 2–3 equivalents of a hydrazine hydrate in presence of substoichiometric amounts of acetic acid.

This reaction occurs rapidly at room temperature with the evolution of nitrogen and the formation of an allylic alcohol.

The final decomposition can proceed by an ionic or a radical pathway, depending on reaction temperature, solvent used, and structure of intermediate 3.

[5] The Wharton olefin synthesis allows the transformation of an α,β unsaturated ketone into an allylic alcohol.

The epoxide starting material can be generated by a number of methods, with the most common being reaction of the corresponding alkene with hydrogen peroxide or m-chloroperoxybenzoic acid.