Benzaldehyde → trans-Stilbene oxide

Participants

Reaction Steps

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%).

Provenance & Evidence