mercury(II) oxide in pentane 2 h; Ambient temperature;

triethylamine; selenium monobromide in dichloromethane T=0°C; 2 h;

disulfur dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=0°C; 2 h; Product distribution; Further Variations:ReagentsTemperatures;

dinitrogen tetraoxide in acetonitrile T=-35°C; 0.166667 h;

triethylamine; selenium monobromide in dichloromethane T=0°C; 2 h;

ethylenediamine; copper(l) chloride in ethanol T=20°C; 24 h;

1.1: hydrogen; palladium 10 on activated carbon / ethanol / 20 °C / 3345.86 Torr 2.1: isopropyl alcohol / 16 h / 20 °C 3.1: isopropyl alcohol 4.1: pyridine / ethyl acetate / 1 h / 20 °C / |Large scale 5.1: camphor-10-sulfonic acid / ethyl acetate / 6 h / |Reflux; |Large scale 5.2: Amberlyst-15 resin / 1 h / |Reflux; |Large scale 6.1: sodium hydroxide / toluene; water / 5 h / 20 °C View Scheme

Cu2Cl2; ammonium hydroxide in dimethyl sulfoxide T=20°C; 4 h;

palladium 10 on activated carbon; hydrogen in ethanol T=20°C; P=3345.86 Torr;