magnesium; mercury dichloride in methanol T=-23°C; 2 h;

2,2'-azo-bisisobutyronitrile in chlorobenzene T=70°C; 22 h;

2,2'-azo-bisisobutyronitrile; t-DDT in chlorobenzene 19 h; Heating;

1: pyridinium p-toluenesulfonate / methanol / 50 °C / |Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane / -78 °C / |Inert atmosphere 3: water; acetic acid / 20 °C / |Inert atmosphere 4: Re2O7; triethylsilane / dichloromethane / 96 h / 20 °C / |Inert atmosphere View Scheme

Multi-step reaction with 2 steps 1.1: n-BuLi / hexane; tetrahydrofuran / -20 °C1.2: 61 percent / PhSTMS / hexane; tetrahydrofuran / 2 h / 0 °C2.1: 88 percent / Raney Ni (W-4) / methanol / 0.5 h / Heating