1: (E)-1-chloro-8-phenyl-1-octene-3,5,7-triyne With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: chloro-trimethyl-silane in tetrahydrofuran; hexane T=-78 - 20°C;

n-butyllithium in hexane T=-78 - -10°C;

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 74 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -30 °C 1.2: 78 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 74 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 92 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 0 - 23 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -30 °C 2.2: 78 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 74 percent / ZnBr2 / Pd(PPh3)4 / tetrahydrofuran; hexane / 6 h / 0 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 55 percent / AlCl3 / CH2Cl2 / 3 h / 0 °C 2: 48 percent / PPh3 / CH2Cl2 / 0.5 h / 20 °C 3: 64 percent / n-BuLi / hexane / -78 - -10 °C View Scheme

1: 48 percent / PPh3 / CH2Cl2 / 0.5 h / 20 °C 2: 64 percent / n-BuLi / hexane / -78 - -10 °C View Scheme