dimethyl diselenide; sodium hydride in N,N-dimethyl-formamide T=130°C; 2 h;

1: With N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 2.5 h; Reflux; 2: With triethylamine in tetrachloromethane T=0°C;

1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran T=-10°C; 0.166667 h;

1: 77.2 percent / KOH / H2O; methanol / 16 h 2: tionyl chloride, dimethylformamide / CH2Cl2 / 1.) 2 h, RT, 2.) 1 h, reflux 3: aluminium chloride / CH2Cl2 / 0.17 h / Ambient temperature 4: Et3N / CHCl3 / 2.5 h View Scheme

1: tionyl chloride, dimethylformamide / CH2Cl2 / 1.) 2 h, RT, 2.) 1 h, reflux 2: aluminium chloride / CH2Cl2 / 0.17 h / Ambient temperature 3: Et3N / CHCl3 / 2.5 h View Scheme

1: 75.7 percent / Zn / benzene / 3 h / Heating 2: 77.2 percent / KOH / H2O; methanol / 16 h 3: tionyl chloride, dimethylformamide / CH2Cl2 / 1.) 2 h, RT, 2.) 1 h, reflux 4: aluminium chloride / CH2Cl2 / 0.17 h / Ambient temperature 5: Et3N / CHCl3 / 2.5 h View Scheme

1: 79 percent / BF3*Et2O / CH2Cl2 / 16 h / -78 deg C to r.t. 2: 91 percent / LiAlH4 / diethyl ether / 0.5 h / Heating 3: 78 percent / 5M H2SO4 / tetrahydrofuran / 2 h / Heating 4: 84 percent / 10percent Pd/C / bis-(2-methoxy-ethyl) ether / 6 h / Heating View Scheme