By Roger A. Sheldon (auth.), Renato Ugo (eds.)

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Extra resources for Aspects of Homogeneous Catalysis

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METAL OXIDE-BASED CATALYSTS-THE EFFECT OF SUPPORTS Mashio and Kato [109,110] studied the epoxidation of l-octene with cumene hydroperoxide or {crt-butyl hydroperoxide in the presence of various metal oxides. Mo0 3 was an excellent catalyst, W0 3 showed moderate activity and other oxides (Y zOs' Se0 2 , Cr0 3 , Cr 2 03' Nb 20 s) gave negligible amounts of epoxide « 10~;»). ). Trifiro and co-workers [9395] examined the activity of various molybdenum *Oxine = X-hydroxyqUInoline. Epoxidations with alkyl hydroperoxides 29 oxide-based catalysts in the epoxidation of cyclohexene with tert-butyl hydroperoxide.

H ~ OH 0 h OH OOR 0 When MoCl s is used as the catalyst it can actually be the HCl formed during reaction which catalyses the ring-opening of the epoxide by R0 2 H [106]. 14. ). However, it is possible to generate the hydroperoxide in situ. For example, the preparation of propylene oxide and cyclohexanol (together with some cyclohexanone) by co-oxidation of cyclohexane and propylene in the presence of molybdenum catalysts has been described [176]. 0+ 0, - OOOH 11071 However, in practice such a procedure has few advantages over the classical two-step procedure and there are disadvantages.

Chong and Sharpless [145], on the other hand, favour a mechanism involving coordination of the oxygen adjacent to the hydrogen of the alkyl hydroperoxide [mechanism (b) or (c)]. There are several points in favour of mechanism(s) (b) and/or (c). In the first place, mechanism (a) requires coordination of the metal to the more hindered oxygen atom of the hydroperoxide. 10. ). The remarkable syn selectivities which are characteristic of these reactions are consistent with a mechanism involving coordination of the allylic alcohol and the hydroperoxide to the same metal atom.

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