ABSTRACT Regiospecifically generated α, β-unsaturated tosylhydrazones dianions are treated with molecular oxygen, yielding α′-hydroxy-α, β-unsaturated tosylhydrazones, versatile intermediates for organic synthesis. They proved to be useful for 1, 2-carbonyl and 1, 2-enone transpositions, and also permitted the preparation of α′-hydroxy enones in very high yields.