0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. 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.

Meeeee 88 Mee(eeeeeeeeeeeeeee)eeeeeeeeeeeeeee(MM) Meeeeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeeeeeeee (%) Meeeeeeeeee (%) eee
M M (MM8)8Me 88 88 [‌88‌]
M M (MM8)88Me 88 88 [‌88‌]
Me 88 88 [‌88‌]