Epoxidation with alkyl hydroperoxides

These reactions, however, have the disadvantage that H202 is usually employed in aqueous solution. It is known that water seriously retards epoxidation, and it may further transform the product epoxides to the corresponding 1,2-diols. This often results in low selectivity, which is the main reason why these reactions do not have the same broad synthetic utility as do epoxidations with alkyl hydroperoxides.245 285... 

Metal oxide-based catalysts were also studied57 in the early days of development of olefin epoxidation with alkyl hydroperoxides. M0O3 was an excellent catalyst, WO3 showed moderate activity and other oxides (V2O5, Se02,... 

Metal-Catalyzed Epoxidation with Alkyl Hydroperoxides 413... 

Metal-catalyzed epoxidations with alkyl hydroperoxides show the following characteristic features [12, 13]. 

Transition Metai-Catalyzed Epoxidation with Alkyl Hydroperoxides. Alkyl hydroperoxides are attractive oxidants on a technical scale because they can be produced by autoxidation of branched alkanes with oxygen. This concept has been realized on the largest scale in the so-called Halcon process, i.e., the transition metal-catalyzed epoxidation of propylene to propylene oxide (35) (Fig. 9). Homogeneous and heterogeneous titanium, vanadium, and molybdenum catalysts are capable of catalyzing the C=C-epoxidation by alkyl hydroperoxide (for a review see Ref. 36). 

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