n-butyllithium; triphenylemethane in tetrahydrofuran T=-78°C; 0.75 h; Yield given;

hydrogen; palladium on activated charcoal in methanol

Lindlar's catalyst Hydrogenation;

1: 62 percent / NBS, CaO, benzoylperoxide / CCl4 / 4.5 h / Heating 2: 56 percent / Dibal / petroleum ether; hexane / 0.22 h / -78 - -50 °C 3: 1.) BuLi; 2.) LDA / 1.) THF, hexane, -85 deg C, 15 min; 2.) THF, -85 deg C, 15 min; 3.) THF, hexane -60 deg C, 30 min 4: Dibal / 1.) ether, petroleum ether, hexane, -70 to -30 deg C, 20 min; 2.) ether, petroleum ether, hexane, acetic acid, -70 to 0 deg C, 45 min 5: 1.) BuLi / 1.) THF, hexane, 0 deg C, then Rt, 15 min; 2.) THF, hexane, Rt, overnight 6: 1.) MnO2; 2.) 96percent H2SO4 / 1.) hexane, Rt, 24 h; 2.) nitromethane, 0 deg C, 15 min View Scheme

lithium aluminium tetrahydride

lithium aluminium tetrahydride

1: 57 percent / m-chlorperbenzoesaeure / CH2Cl2 / 2 h / Heating 2: Amberlite IR-120 / tetrahydrofuran; H2O / 4.5 h / Ambient temperature View Scheme

1: liquid ammonia 2: H2 / Lindlar / benzene View Scheme

sodium hypobromide

benzoic acid in benzene