1: With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-100°C; 0.75 h; 2: With iodine in tetrahydrofuran; hexane T=-75°C; 0.25 h;

iodine cloride

1: 98 percent / H2NNH2*H2O / tetrahydrofuran / 2 h / 50 °C 2: 89 percent / CuSO4*5H2O / H2O / 2 h / Heating 3: 93 percent / ICl View Scheme

1: 89 percent / CuSO4*5H2O / H2O / 2 h / Heating 2: 93 percent / ICl View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -100 °C 1.2: 84 percent / tetrahydrofuran; hexane / cooling 2.1: 98 percent / H2NNH2*H2O / tetrahydrofuran / 2 h / 50 °C 3.1: 89 percent / CuSO4*5H2O / H2O / 2 h / Heating 4.1: 93 percent / ICl View Scheme

1.1: 51 percent / CuSO4*5H2O / H2O / 0.42 h / Heating 2.1: (i-Pr)2NH; BuLi / tetrahydrofuran; hexane / 0.75 h / -100 °C 2.2: 82 percent / I2 / tetrahydrofuran; hexane / 0.25 h / -75 °C View Scheme

1: With lithium diisopropyl amide in tetrahydrofuran 2.5 h; 2: With water in tetrahydrofuran