Hydrogen Peroxide → (R,R)-Stilbene oxide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To 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%).

Herkunft & Nachweise