[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].ClCCl.[OH:14]O>O.[O-2].[O-2].[Mn+4]>[CH2:1]1[O:14][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
In a 25 mL scintillation vial equipped with a magnetic stirrer, 1-decene (1.41 g, 10 mmol) was placed followed by addition of 4 mL dichloromethane. To this solution was added BTSP (2.8 g, 15 mmol). The vial was immersed into ice/water bath. After 5 minutes Re2O7 (24 mg, 0.05 mmol)5 was added followed by 10 μL of water. The reaction turned bright yellow and was allowed to warm up to room temperature and stirred for 14 h. Upon completion, water (3 drops) was added followed by manganese dioxide (ca. 5 mg) in order to decompose the remaining H2O2. The destruction of H2O2 was evident by the disappearance of yellow color. The mixture was then dried over Na2SO4. Concentration afforded 1-decene oxide (1.48 g, 94% yield) of a colorless oil.
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