FeBr2 in toluene T=140°C; 16 h; Schlenk techniqueInert atmosphere;

1: sec.-butyllithium With zinc dibromide in tetrahydrofuran T=0°C; 0.166667 h; Inert atmosphere; 2: With zinc dibromide in tetrahydrofuran T=25°C; 0.166667 h; Inert atmosphere; 3: Br-BDT With chloro-trimethyl-silane in tetrahydrofuran T=-60 - 125°C; Inert atmosphereMicrowave irradiation; regioselective reaction;

in acetic acid 2 h; Heating;

1: diisobutylaluminium hydride / toluene / 20 °C / |Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / |Inert atmosphere 3: iron; acetic acid / ethanol / 2 h / 80 °C / |Inert atmosphere 4: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 5: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / |Inert atmosphere 2: iron; acetic acid / ethanol / 2 h / 80 °C / |Inert atmosphere 3: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 4: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

1: iron; acetic acid / ethanol / 2 h / 80 °C / |Inert atmosphere 2: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 3: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

1: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 2: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

Daucus carota; dihydrogen peroxide in various solvent(s) T=25°C; 18 h;