[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(C)=[O:20])(F)(F)F.OO>C([O-])([O-])=O.[K+].[K+]>[CH:4]1[CH:3]=[CH:2][C:1]([C@H:7]2[O:20][C@@H:8]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1To a mixture of suspension of trans-stilbene (18.02 g, 0.1 mol) and CF3COCH3 (3.36 g, 0.03 mol) in CH3CN-DMM (½ v/v, 750 mL) and aqueous K2CO3 (1.5 M in 4×10−4 M EDTA, 150 mL) was added H2O2 (30%, 40 mL, 0.4 mol) at 0° C. Upon stirring at 0° C. for 1 h and at room temperature for 5 h, the reaction mixture was extracted with hexane (3×500 mL). The combined organic layers were washed with aqueous Na2S2O3 (1 M) (3×50 mL) and brine (100 mL), dried (Na2SO4), filtered, concentrated, and purified by flash chromatography on silica gel (buffered with 1% NEt3) using hexane-ether as eluent to give trans-stilbene oxide as a white solid (18.3 g, 93.3%).
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