1: 90 percent / diethyl ether / 10 h / 10 - 15 °C 2: 54 percent / sodium borohydride / H2O / 0.5 h / Ambient temperature View Scheme

triethylsilane; palladium dichloride in ethanol 1 h; Inert atmosphereReflux;

toluene-4-sulfonic acid 4 h; Heating;

sodium tetrahydroborate; N,N,N',N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine in tetrahydrofuran T=25°C; 1.5 h; Inert atmosphere;

1: 90 percent / diethyl ether / 10 h / 10 - 15 °C 2: 54 percent / sodium borohydride / H2O / 0.5 h / Ambient temperature 3: 30 percent / hydrogen / PtO2 / methanol / 1 h / 2068.6 Torr / Ambient temperature 4: 60 percent / 10percent aq. sulfuric acid / 7 h / Ambient temperature View Scheme

1: 1.) CuI, (CH3)2S / 1.) THF, -20 deg C, 10 min, 2.) THF, -20 deg C, 15 min 2: S8 / decahydronaphthalene / 3 h / Heating 3: oxalic acid / H2O / 1 h / Heating View Scheme