Abstract The reactions of six hydrazones with bromine in the presence of pyridine, and of two hydrazones with chlorine under a variety of conditions, were investigated. Geminal dihalides, haloalkenes, rearranged products, azines, and carbonyl compounds account for up to 85% of the products of the reaction with bromine, but the reactions with chlorine give rise to more complex mixtures. The mechanisms of these reactions are discussed and ...