Styrene → (R,R)-Stilbene oxide

HRID 1516957Notes

Reaction equation

HRID 1516957 reaction equation
C=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:9]1[CH:14]=[C:13](Cl)[CH:12]=[C:11]([C:16]([O:18]O)=O)[CH:10]=1>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH:6]1[CH:5]=[CH:4][C:3]([C@H:2]2[O:18][C@@H:16]2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:9][CH:10]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7501StyreneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 185583(R,R)-Stilbene oxideYield 83%

Reagents, catalysts & solvents 1

HCID 178425456HCID 178425456, compoundCatalyst

Procedure

Reaction of styrene with Grubbs' second generation catalyst for 6 hours, followed by reaction of the subsequent product with 5 equivalents of site-isolated MCPBA for 14 hours gave trans-stilbene oxide in 83% yield. The 1H and 13C NMR spectra agreed with those reported in the literature. 1H NMR (CDCl3): 7.33-7.38 (m, 10H), 3.87 (s, 213C NMR (CDCl3): 62.81, 125.47, 128.29, 128.53, 137.07.

Sources & evidence

ORD record
ord-922a985b0b4b494195f5f43060b293b0
Source dataset
uspto-grants-2012_07
Patent number
US08227635B2

Reaction notes

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