Abstract
RECENT investigations on the peroxide-induced reactions of cyclic ethers with 1-octene have demonstrated that ketones are the major reaction products formed1,2. Mechanistically, these reactions involve a free-radical decomposition or re-arrangement of the α-ethereal radical initially formed and subsequent addition to the olefine to give the products observed. In a logical extension of these studies we have investigated the free radical chemistry of a cyclic diether, p-dioxane, and a cyclic aminoether, morpholine. In the case of p-dioxane it was of interest to determine if cyclic diethers of this general type behave in a manner similar to tetrahydropyran. Morpholine is of interest since it allows one to estimate the reactivity of the two types of α-carbon hydrogen bonds (α-ethereal versus α-amino) toward peroxy radicals in a cyclic system.
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