1: 94 percent / 1.) KOH / dimethylsulfoxide / 1.) RT, 90 min, 2.) RT, 4 h 2: 90 percent / benzene; acetone / 10 h / Ambient temperature 3: 88 percent / H2 / PtO2 / ethanol; H2O / 40 °C / 760 Torr 4: 15 percent / 1.) Hg(Ac)2, aqu. 5percent AcOH, 2.) H2S, 3.) K2CO3, NaBH4 / 1.) reflux, 4 h, 2.) 1 h, 90 deg C, 3.) aqu. AcOH, EtOH, RT, 1 h View Scheme

1: 94 percent / 1.) KOH / dimethylsulfoxide / 1.) RT, 90 min, 2.) RT, 4 h 2: 90 percent / benzene; acetone / 10 h / Ambient temperature 3: 88 percent / H2 / PtO2 / ethanol; H2O / 40 °C / 760 Torr 4: 15 percent / 1.) Hg(Ac)2, aqu. 5percent AcOH, 2.) H2S, 3.) K2CO3, NaBH4 / 1.) reflux, 4 h, 2.) 1 h, 90 deg C, 3.) aqu. AcOH, EtOH, RT, 1 h View Scheme

1: 90 percent / benzene; acetone / 10 h / Ambient temperature 2: 88 percent / H2 / PtO2 / ethanol; H2O / 40 °C / 760 Torr 3: 15 percent / 1.) Hg(Ac)2, aqu. 5percent AcOH, 2.) H2S, 3.) K2CO3, NaBH4 / 1.) reflux, 4 h, 2.) 1 h, 90 deg C, 3.) aqu. AcOH, EtOH, RT, 1 h View Scheme

1: 88 percent / H2 / PtO2 / ethanol; H2O / 40 °C / 760 Torr 2: 15 percent / 1.) Hg(Ac)2, aqu. 5percent AcOH, 2.) H2S, 3.) K2CO3, NaBH4 / 1.) reflux, 4 h, 2.) 1 h, 90 deg C, 3.) aqu. AcOH, EtOH, RT, 1 h View Scheme

sodium tetrahydroborate; hydrogen sulfide; mercury(II) diacetate; potassium carbonate; acetic acid 1.) reflux, 4 h, 2.) 1 h, 90 deg C, 3.) aqu. AcOH, EtOH, RT, 1 h; Yields of byproduct given;