Abstract
Cyclohexene and 1-octene have been epoxidized in the liquid phase with tert-butyl hydroperoxide in the presence of a wide variety of transition-metal catalysts. The reactions occurring in these systems involve competing metal-catalyzed epoxidation and metal-catalyzed homolytic decomposition of the hydroperoxide. Subsequent reactions of the radicals produced in the latter reaction are responsible for the formation of many of the by-products observed. It is concluded that an active epoxidation catalyst should be both a weak oxidant and a fairly strong Lewis acid. These requirements are best met by compounds of certain metals in high oxidation states [Mo(VI), W(VI), Ti(IV)]. Many of the epoxidations described are subject to autoretardation by the co-product tert-butanol, the extent of which increases in the order W < Mo < Ti < V.
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