potassium fluoride; anhydrous tetramethylammonium chloride in dimethyl sulfoxide T=150°C; 6 h;

1.1: 79 percent / aq. CuSO4 / Heating 2.1: BuLi / tetrahydrofuran; hexane 2.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 3.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme

1.1: 65 percent / aq. CuSO4 / Heating 2.1: 68 percent / hydrazine monohydrate / ethanol / 6 h / Heating 3.1: 79 percent / aq. CuSO4 / Heating 4.1: BuLi / tetrahydrofuran; hexane 4.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 5.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme

1.1: 88 percent / hydrazine monohydrate / ethanol / 2 h / Heating 2.1: 65 percent / aq. CuSO4 / Heating 3.1: 68 percent / hydrazine monohydrate / ethanol / 6 h / Heating 4.1: 79 percent / aq. CuSO4 / Heating 5.1: BuLi / tetrahydrofuran; hexane 5.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 6.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme

1.1: 90 percent / Zn; aq. ammonia / 6 h / 0 °C 2.1: 88 percent / hydrazine monohydrate / ethanol / 2 h / Heating 3.1: 65 percent / aq. CuSO4 / Heating 4.1: 68 percent / hydrazine monohydrate / ethanol / 6 h / Heating 5.1: 79 percent / aq. CuSO4 / Heating 6.1: BuLi / tetrahydrofuran; hexane 6.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 7.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme

1.1: 68 percent / hydrazine monohydrate / ethanol / 6 h / Heating 2.1: 79 percent / aq. CuSO4 / Heating 3.1: BuLi / tetrahydrofuran; hexane 3.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 4.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane 1.2: 73 percent / hexachloroethane / tetrahydrofuran; hexane 2.1: 51 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 6 h / 150 °C View Scheme