1: 2,5-diiodo-1,4-bis(n-octyloxy)benzene With n-butyllithium in diethyl ether T=0°C; 0.25 h; 2: N,N-dimethyl-formamide in diethyl ether T=0 - 20°C; 2 h;

1: 90 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 2: 59 percent / I2; KIO3; aq. H2SO4 / acetic acid / 24 h / 80 °C 3: 85 percent / BuLi / tetrahydrofuran; diethyl ether / 2.5 h / 0 °C View Scheme

1: KOH / dimethylsulfoxide 2: I2; IO3- 3: n-BuLi View Scheme

1: 59 percent / I2; KIO3; aq. H2SO4 / acetic acid / 24 h / 80 °C 2: 85 percent / BuLi / tetrahydrofuran; diethyl ether / 2.5 h / 0 °C View Scheme

1.1: 90 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 2.1: 63 percent / I2; KIO3; H2SO4 / acetic acid / 12 h / 80 °C 3.1: n-BuLi / diethyl ether / 0.25 h / 0 °C 3.2: 85 percent / diethyl ether / 2 h / 0 - 20 °C View Scheme