1: 85 percent / Br2 2: 2.) butanethiol, sodium hydride, 3.)HgSO4 / 1.) CH2Cl2, reflux, 24h, 2.) ether, room temp., 24h, reflux, 24h, 3.) 1h View Scheme

bromine

tert.-butylhydroperoxide; titanium silicate 24 h; Heating;

tert.-butylhydroperoxide; titanium silicate 24 h; Heating;

Ti-β titanium silicate in tetrahydrofuran T=59.84°C; 16 h;

1: 36 percent / oxygen / palladium diacetate / dimethylsulfoxide / 1 h / 40 °C / 760 Torr 2: 65 percent / iodine; pyridine / CCl4 / 0 - 20 °C 3: triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 4: 89 percent / hydrogen / palladium on carbon / methanol / 0.5 h / 20 °C / 760 Torr View Scheme

oxygen; palladium diacetate in dimethyl sulfoxide 6 h; Ambient temperature;

palladium diacetate in hexane-water; water

in hexane-water; water; dimethyl sulfoxide