1: 1,4-diiodo-2,5-dioctyl-benzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78°C; 2 h;

trifluoroacetic acid in water Heating;

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -60 °C 1.2: tetrahydrofuran; hexane / 1 h / -60 - 20 °C 2.1: p-toluenesulfonic acid / benzene / 5 h / Heating 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 3.2: tetrahydrofuran; hexane / -70 - 20 °C 4.1: p-toluenesulfonic acid / benzene / 2 h / Heating 5.1: 91 percent / trifluoroacetic acid / H2O / Heating View Scheme

1.1: p-toluenesulfonic acid / benzene / 5 h / Heating 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 2.2: tetrahydrofuran; hexane / -70 - 20 °C 3.1: p-toluenesulfonic acid / benzene / 2 h / Heating 4.1: 91 percent / trifluoroacetic acid / H2O / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 1.2: tetrahydrofuran; hexane / -70 - 20 °C 2.1: p-toluenesulfonic acid / benzene / 2 h / Heating 3.1: 91 percent / trifluoroacetic acid / H2O / Heating View Scheme

1: p-toluenesulfonic acid / benzene / 2 h / Heating 2: 91 percent / trifluoroacetic acid / H2O / Heating View Scheme