tributyl-amine; hydrogen; palladium on activated charcoal in benzene 6 h; Ambient temperature;

titanium tetrachloride in chloroform T=-20°C; 0.75 h;

in trifluoroacetic acid T=80°C;

magnesium in N,N-dimethyl-formamide byproducts: Mg(2+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), organic phase dried over sodium or magnesium sulfate and concentrated under vacuum, side product phenol formation avoided by work-up under inert atmosphere;

in water-d2; dimethyl sulfoxide T=37°C; pH=5.5; 2-[N-morpholino]ethanesulfonic acid (MES) buffer; Product distribution / selectivity;

aluminium trichloride; hydrogen; palladium on activated charcoal 1.) tetrachloroethane, rt, 30 min; 2.) 100 deg C, normal pressure or 50 deg C, 30 atm; AcONa can be added; Multistep reaction;

ethanol; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; water

sodium acetate; copper(II) sulfate; sodium sulfite anschliessenden Erhitzen mit wss.HCl;

(i) SnCl4, CH2Cl2, (ii) aq. NaHSO3; Multistep reaction;

1: 80 percent / NaBH4 / tetrahydrofuran / 2 h / 0 °C 2: 70 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C View Scheme