N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 2 h; Inert atmosphereReflux;

1,1-Diiodoethane; tert.-butyl lithium in tetrahydrofuran

1: N2H4*H2O / acetic acid 2: N2H4*H2O / Pd-C 3: (i) NaNO2, aq. HCl, (ii) aq. KI View Scheme

1: H2SO4, KNO3 2: N2H4*H2O / acetic acid 3: N2H4*H2O / Pd-C 4: (i) NaNO2, aq. HCl, (ii) aq. KI View Scheme

1.1: dibromocyanuric acid; H2SO4 / 15 h / 0 - 20 °C 1.2: 54 percent / NaBH4; BF3*OEt2 / tetrahydrofuran 2.1: 97 percent / oxalyl chloride; dimethylsulfoxide / CH2Cl2 / 1.3 h / -60 °C 3.1: 96 percent / hydrazine monohydrate / acetic acid / 2.5 h 4.1: 67 percent / tert-butyllithium; diiodoethane / tetrahydrofuran View Scheme

1: 97 percent / oxalyl chloride; dimethylsulfoxide / CH2Cl2 / 1.3 h / -60 °C 2: 96 percent / hydrazine monohydrate / acetic acid / 2.5 h 3: 67 percent / tert-butyllithium; diiodoethane / tetrahydrofuran View Scheme

1: 96 percent / hydrazine monohydrate / acetic acid / 2.5 h 2: 67 percent / tert-butyllithium; diiodoethane / tetrahydrofuran View Scheme

1: N2H4*H2O / Pd-C 2: (i) NaNO2, aq. HCl, (ii) aq. KI View Scheme

(i) NaNO2, aq. HCl, (ii) aq. KI; Multistep reaction;