copper(II) sulfate in dichloromethane T=20°C; 0.0833333 h;

tetra-n-butylammonium tribromide in tetrahydrofuran T=20°C; 0.75 h;

tetra-n-butylammonium tribromide in tetrahydrofuran T=20°C; 0.75 h;

Kaolinitic clay in tetrachloromethane 4 h; Heating;

n-butyllithium; oxygen 1.) THF, -70 deg C, 10 min, 2.) THF, room temp., 10 min; Yield given. Multistep reaction;

n-butyllithium; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) THF, -70 deg C, 10 min, 2.) THF, room temp., 1 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 85 percent / NaBH4 / 5percent Pd/C / tetrahydrofuran; H2O / 18 h / 20 °C 2: 86 percent / tetrahydrofuran / 5 h / Heating 3: 73 percent / NaH / various solvent(s); dimethylformamide / 2 h / 20 °C View Scheme

N-benzyl-DABCO tribromide in methanol; dichloromethane T=20°C; 0.05 h;

1.1: 80 percent / iron; ammonium chloride / H2O; ethanol / 2.83 h / Heating 2.1: HCl; sodium nitrite / H2O / 0.5 h / 0 - 5 °C 2.2: potassium ethyl xanthate / H2O / 0.5 h / 40 - 45 °C 2.3: 64 percent / LiAlH4 / tetrahydrofuran 3.1: 65 percent / pyridine / CH2Cl2 / 20 °C 4.1: titanocene dichloride; magnesium; triethyl phosphite / tetrahydrofuran / 0.25 h 4.2: 35 percent / tetrahydrofuran View Scheme

1: 85 percent / NaBH4 / 5percent Pd/C / tetrahydrofuran; H2O / 18 h / 20 °C 2: 86 percent / tetrahydrofuran / 5 h / Heating 3: 86 percent / LDA / tetrahydrofuran; heptane; ethylbenzene / 1.75 h / -78 - 20 °C View Scheme