By Roger A. Sheldon (auth.), Renato Ugo (eds.)
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Extra info for Aspects of Homogeneous Catalysis
4. 1. , were the most effective catalysts. g. molybdenum metal [107,108], Mo0 3 [75,81,109,110] and molybdic acid [75,81], their activity was generally assumed to result from their dissolution in the presence of the hydroperoxide. The implication was that the reaction occurs in the liquid phase and involves homogeneous catalysis. Thus, in the original examples  metal oxides, such as Mo0 3 , were usually given a pretreatment step in which the oxide was heated with tert-butyl hydroperoxide in tert-butanol, in order to effect solubilization of the catalyst.
1,2-Cyclohexanediol and epoxycyclohexane also increased the rate and reduced the induction period but to a lesser extent than HMPA. It was demonstrated that a soluble complex is formed by reaction of the three components: Mo0 3 , ROzH and HMPA. Addition of bipyridine to the solution of the three components resulted in the precipitation of the peroxo complex (V). (V) On the basis of these results a metal-peroxide type mechanism was proposed which involved the intermediacy of MoOs (HMPA) (see Section 3), formed from Mo0 3 , R0 2 H and HMPA (cf.
The directing effect of hydroxyl groups was utilized to effect remote epoxidations of specific double bonds in steroid and terpene molecules. The principle is illustrated by the example below. TBHP Ma(CO). (103) • (XXXVJJ) (XXXVII]) TBHP Mo(CO). ~...... o o~oo (XXXIX) (XL) Compound (XXXVII) undergoes stereoselective allylic epoxidation to produce (XXXVIII) with Mo(CO)6 /TBHP. In contrast, the addition of the template to produce (XXXIX) directs the reagent to give regio- and stereoselective epoxidation at the remote double bond.
Aspects of Homogeneous Catalysis by Roger A. Sheldon (auth.), Renato Ugo (eds.)