1: (i) nBuLi, (ii) /BRN= 2461289/ 2: Li, EtNH2 / tetrahydrofuran / -78 °C View Scheme

anhydrous lithium acetate; copper diacetate; copper T=85 - 90°C;

anhydrous lithium acetate; copper diacetate; copper T=85 - 90°C;

anhydrous lithium acetate; copper diacetate; copper T=85 - 90°C;

1: [(E)-3,7-dimethylocta-2,6-dienyl](phenyl)sulfane With LiDBB in tetrahydrofuran T=-78°C; 2: chloro-trimethyl-silane in tetrahydrofuran T=-78°C; 0.0833333 h;

lithium 1.) THF, -78 deg C, 2.) NH3, -78 deg C; Yield given. Multistep reaction;

1: 1) n-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) THF, -50 deg C, 1 h; 2) THF, -40 deg C to room temp. within 1 h, then 10 h 2: 69 percent / Me2S/SO2Cl2, Et3N / CH2Cl2 / 2 h / -40 °C 3: tetrahydrofuran / 1 h at -65 deg C, then 19 h at room temp. 4: 70 percent / Na, liquid NH3 / diethyl ether / 0.33 h / -60 °C View Scheme