Dimethyl Sulfide → 1-Benzoyl-2,3-diphenylcyclopropane

Participants

Reaction Steps

Phenyl diazomethane (prepared as in Example 36, 0.5 mmol in 3 ml of t-butyl methyl ether) was added to a stirred solution of dimethylsulphide (7.3 ml; 0.1 mmol), rhodium (II) acetate (2 mg; 0.005 mmol) and chalcone (103 mg; 0.5 mmol) in dichloromethane (2 ml) at room temperature over a period of 24 hours. After the addition was complete the solvent was removed in vacuo and the residue was chromatographed over silica [eluent dichloromethane:petrol (2:3)], to give the title compound as a 4:1 mixture of trans:cis cyclopropanes as a yellowy solid (58 mg; 39%).

Provenance & Evidence