A new technique has been used for the autoxidation of isopropylbenzene t o give aa-dimethylbenzyl hydroperoxide. An alkaline (pH 8-5-10-5) oil-in-water emulsion of the hydrocarbon absorbs oxygen at 85' to give a good yield of the hydroperoxide identical with that previously reported by Hock and Lang (Ber., 1944, 77, 257). The characteristics of the autoxidation are consistent with a radical-chain mechanism.

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Olefins of various structures have been oxidized with oxygen at 85–125°, generally in the presence of mild alkali and a catalyst, and the products examined. These products were complex mixtures and appeared to have been derived from attack at several positions in the molecule. All except one of these olefins provided epoxides as major products; the one exception, 2:2:5:5‐tetra‐methylhex‐3‐ene, was structurally incapable of forming a hydroperoxide at the allyl position.