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37.2.1.3.2 Method 2: Molybdenum-Mediated Epoxidation with Alkyl Hydroperoxides

DOI: 10.1055/sos-SD-037-00140

Adolfsson, H.Science of Synthesis, (200837242.

Hexacarbonylmolybdenum(0) has been used in combination with tert-butyl hydroperoxide for the epoxidation of terminal alkenes.[‌35‌] Good yields and selectivity for the epoxide products are obtained when reactions are performed under anhydrous conditions in hydrocarbon solvents such as benzene. The inexpensive and considerably less toxic bis(acetylacetonato)dioxomolybdenum(VI) is a robust alternative to hexacarbonylmolybdenum(0).[‌57‌] A number of different substrates ranging from simple α-alkenes to more complex terpenes have been oxidized using a very low catalytic loading of this particular molybdenum complex (Scheme 17). The epoxidations are carried out using dry tert-butyl hydroperoxide (70%) in toluene.

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