cesium fluoride; tris(dibenzylideneacetone)dipalladium (0) in acetonitrile T=20°C;

iodine; methyloxirane in benzene 21 h; Irradiation;

iodine in benzene Irradiation;

1: 70 percent / tetrahydrofuran; hexane / -70 deg C, 1 h, -70 deg C to room temperature, 2 h, room temperature, 1 h 2: 1.) DDQ, 2.) p-TsOH / 1.) benzene, reflux, 1.5 h, 2.) reflux, 2 h 3: 96 percent / iodine, propylene oxide / benzene / 21 h / Irradiation View Scheme

1: 1.) DDQ, 2.) p-TsOH / 1.) benzene, reflux, 1.5 h, 2.) reflux, 2 h 2: 96 percent / iodine, propylene oxide / benzene / 21 h / Irradiation View Scheme