Summary
It has been shown that certain alkylbenzenes having a hydrogen atom on the alpha carbon atom react with maleic anhydride to form compounds analogous to the hydroperoxides produced by autoxidation of the alkylbenzenes. The structure of these products has been determined by oxidation with aqueous permanganate and the results have been applied, together with other data, to demonstrate that the reaction proceeds by a free radical chain mechanism involving the abstraction of a hydrogen atom from the alpha carbon atom. In view of the analogy between the products obtained in this investigation and in autoxidation, it is suggested that autoxidation is propagated in a similar manner.
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One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural and Research Administration, U. S. Department of Agriculture.
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Bickford, W.G., Fisher, G.S., Dollear, F.G. et al. Autoxidation of fats. I. Preparation and oxidation of alkylbenzene-maleic anhydride adducts. J Am Oil Chem Soc 25, 251–254 (1948). https://doi.org/10.1007/BF02593477
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DOI: https://doi.org/10.1007/BF02593477