1,8-diazabicyclo[5.4.0]undec-7-ene T=140°C; 12 h;

sodium tetrahydroborate; nickel dichloride in tetrahydrofuran T=20°C; 0.75 h;

[Co(PPh3)3Cl] in benzene 1 h; Ambient temperature; Yield given. Yields of byproduct given;

1: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 12 h / 140 °C 2: 71 percent / LAH / diethyl ether / 4 h 3: 53 percent / KH, 1,3-diaminopropane / 3.5 h / 0 - 20 °C View Scheme

1: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 12 h / 140 °C 2: 71 percent / LAH / diethyl ether / 4 h 3: 53 percent / KH, 1,3-diaminopropane / 3.5 h / 0 - 20 °C 4: 60 percent / CrO3, H2SO4 / acetone / 16 h / 10 °C 5: 88 percent / diethyl ether / 10 h / 0 °C 6: 1.) catecholborane, H2O, 2.) NaI, chloramine-T / 1.) 18 h, 2.) THF, H2O, 15 min View Scheme