1: 70 percent / sodium, mercaptoethanol, water / methanol / 2.5 h / Heating 2: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating View Scheme

ammonium sulfate; mercury(II) cyanide; 1,1,1,3,3,3-hexamethyl-disilazane 1.) 2 h, reflux; 2.) benzene, 3 h, reflux; Yield given. Multistep reaction;

1: 98 percent / 5percent Pd/C, H2, anhydrous sodium acetate / ethanol / 18 h / 2068.6 Torr / Ambient temperature 2: 70 percent / 1N BCl3 / CH2Cl2 / 1.) -78 deg C, 3 h; 2.) r.t., 1 h View Scheme

palladium on activated charcoal; hydrogen; sodium acetate in ethanol P=2068.6 Torr; 18 h; Ambient temperature;