Hydrogen Peroxide → (R,R)-Stilbene oxide

HRID 650281Notes

Reaction equation

HRID 650281 reaction equation
[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.[OH:15]O>C1COCC1.O.[O-2].[O-2].[Mn+4]>[CH:4]1[CH:3]=[CH:2][C:1]([C@H:7]2[O:15][C@@H:8]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 638088trans-Stilbene

Product 1

HCID 185583(R,R)-Stilbene oxideYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 25 mL scintillation vial equipped with a magnetic stirrer, trans-stilbene (1.80 g, 10 mmol) was placed followed by addition of 2.8 mL THF.6 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) was added dropwise as a solution in 1.2 mL THF.7 The reaction turned yellow and was allowed to warm up to room temperature and stirred for 10 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 trans-stilbene oxide (1.88 g, 96% yield) of as an off-yellow solid.

Workup

  1. customIn a 25 mL scintillation vial equipped with a magnetic stirrer
  2. addition6 To this solution was added BTSP (2.8 g, 15 mmol)
  3. customThe vial was immersed into ice/water bath
  4. customThe destruction of H2O2
  5. dry with materialThe mixture was then dried over Na2SO4
  6. concentrationConcentration

Sources & evidence

ORD record
ord-d23b4f07d04b4318b7cf18a484905633
Source dataset
uspto-grants-2001_08
Patent number
US06271400B1

Reaction notes

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