pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, a) -50 deg C, 1 h, b) room temperature, 14 h, 2) -40 deg C to room temperature; Yield given. Multistep reaction;

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1: SOCl2 / Heating View Scheme

pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, room temperature, 14 h, 2) THF, room temperature, 24 h; Yield given. Multistep reaction;

pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, room temperature, 24 h, 2) THF, room temperature, 24 h; Yield given. Multistep reaction;

pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, room temperature, 14 h, 2) room temperature, 10 h; Yield given. Multistep reaction;

pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, room temperature, 24 h, 2) THF, room temperature, 24 h; Yield given. Multistep reaction;

1: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 2: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 3: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 4: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 5: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 6: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 7: 82 percent / dimethylformamide / Ambient temperature; overnight 8: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 9: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 2: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 3: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 4: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 5: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 6: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 7: 82 percent / dimethylformamide / Ambient temperature; overnight 8: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 9: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: diethyl ether / -5 °C 2: LiAlH4 / diethyl ether 3: SOCl2, Py / diethyl ether / -10 °C 4: (i) Mg, I2, Et2O, (ii) /BRN= 1900390/ View Scheme