Benzaldehyde → 2,3-Diphenyl-oxirane

HRID 1941476Notes

Reaction equation

HRID 1941476 reaction equation
[C:1]1([CH:7]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:1]1([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C@H:7]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 136601Benzene, (diazomethyl)-HCID 178418361HCID 178418361, compound

Product 2

HCID 915042,3-Diphenyl-oxiraneYield 16%HCID 985111689-71-0Yield 1.5%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of phenyldiazomethane (1 mmol in 6 ml of t-butyl methyl ether) was added, over a period of 12 hours, to a solution of a sulphide of formula (C) wherein R' and R" are both hydrogen (for preparation see J. Org. Chem. 44 (20) 3598-9 (1979); 198 mg, 1.0 mmol), rhodium (II) acetate (4 mg, 0.01 mmol) and benzaldehyde (190 μl, 1.0 mmol) in dichloromethane (4 ml). Upon completion of the addition, the solvent was removed in vacuo and the residue chromatographed using silica gel eluting with dichloromethane:petrol 40:60 to yield trans-2,3-diphenyl oxirane (31 mg, 16%, 51%ee) and cis-2 3-diphenyl oxirane (3 mg, 1.5%).

Workup

  1. additionUpon completion of the addition
  2. customthe solvent was removed in vacuo
  3. customthe residue chromatographed

Sources & evidence

ORD record
ord-edc60f3aa0d04dd4ab6f660b652aa2b3
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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