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1: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 2: 27 percent / H2O / 5 h / 160 °C 3: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 4: 58 percent / piperidine / ethanol / 18 h / Heating 5: 61 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide / 42 h / Ambient temperature 6: 98 percent / 2N aq. HCl / methanol / 2 h / Heating View Scheme

sodium tetrahydroborate in ethanol T=0°C; 1.5 h;

1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C 2: 10percent aq. H2SO4 / 2 h / Heating 3: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C View Scheme

1: 10percent aq. H2SO4 / 2 h / Heating 2: 90 percent / NaBH4 / ethanol / 1.5 h / 0 °C View Scheme

water; bromine T=100°C;

hydrogenchloride; iodine; chlorine

sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide 1.) THF, 65 deg C, 9 h; other vinyl and propenyl heterocycles; other pyridine-BF3 complexes; other hydroborating agents; var. temp. and time; Product distribution;