1: 77 percent / H2 / Lindlar catalyst / ethanol 2: 62 percent / CBr4; PPh3 / CH2Cl2 / 3 h / 20 °C View Scheme

1: 86 percent / NaBH4; H2; ethandiamine / Ni(OAc)2*4H2O / ethanol / 20 °C 2: PBr3; pyridine / diethyl ether / 0.5 h / -30 °C View Scheme

pyridine; phosphorus tribromide in diethyl ether T=-10°C; 0.5 h; Title compound not separated from byproducts.;

pyridine; phosphorus tribromide in diethyl ether T=-30°C; 0.5 h; Title compound not separated from byproducts.;

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C 1.2: -78 - 20 °C 2.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Inert atmosphere; Reflux 3.1: phosphorus tribromide / diethyl ether / 1 h / 0 °C / Inert atmosphere View Scheme

di-tert-butyl peroxide in benzene IrradiationΗrctn; Rate constantThermodynamic data;

dilithium tetrachlorocuprate in tetrahydrofuran; ethylene glycol dimethyl ether T=0 - 20°C; Grignard reaction; 18.75 h; optical yield given as percent de;