COMMUNICATIONS
Experimental Section16. To a solution of 15 (92 mg, 0.072 mmol) in chloroform/methanol 112 (80 mL) was added 1 M NaOCHJCH,OH (2 mL, 2 mmol). This was held at reflux for 4 h under argon in the dark. After removal of the solvent and drying, the residue was purified by preparative thin layer chromatography (neutral Al,O,, CH,Cl,, exclusionoflight;R,of 16isabout 1).Afterdryingat40"C/10~2Torr,64mgof 16was obtained (0.056 mmol, 77%). 17: All reactions were carried out in a glove box under argon. Iron complex 15 (0.56 mg. 4 x lo-' mol) and crown complex 18 (16 mg, 21.2 x mol) were dissolved in DMSO (4 mL) and allowed to react for 30 min. After the addition of a DlMSYLNa solution (31 -44 mg NaH) and a further 30 min reaction, the volume of the solution was increased to 20 mL, and CO was bubbled through the solution. Epoxidation of cis-stilbene (under argon with light exclusion): cis-stilbene (450 mg, 2.5 rnmol), 16 (28.8 mg, 0.025 mmol), and iodosylbenzene (55 mg, 0.25 mmol) were stirred in CH,Cl, (6 mL) for 5 h at room temperature. After removal of the solvent (30 'C, 300 mbar), the residue was taken up in 200 rnL n-pentane, and the catalyst removed by filtration (25-30% 16 was recovered unchanged); the solvent was then removed (30°C 300 mbar). Quantitative analysis of the reaction products was carried out by 'H NMR spectroscopy with 4-chlorotoluene as internal standard.
