selenium; alpha-chloronaphthalene T=280°C;

1: 82 percent / AlCl3 / CS2 / 6 h / 0 °C 2: 100 percent / NaBH4 / ethanol; H2O / 20 h / Ambient temperature 3: 71 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4: 70 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating 5: 58 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 2.5 h / Heating View Scheme

1: sulfur / 240 °C 2: sodium; diethyl ether / anschliessend Behandeln mit Methanol View Scheme

With  aluminium trichloride in  dichloromethane 4 h;  Ambient temperature;   

Multi-step reaction with 4 steps 1: 82 percent / AlCl3 / CS2 / 6 h / 0 °C2: 100 percent / NaBH4 / ethanol; H2O / 20 h / Ambient temperature3: 71 percent / p-toluenesulfonic acid / benzene / 2 h / Heating4: 70 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating  

Multi-step reaction with 3 steps 1: 82 percent / AlCl3 / CS2 / 6 h / 0 °C2: 100 percent / NaBH4 / ethanol; H2O / 20 h / Ambient temperature3: 71 percent / p-toluenesulfonic acid / benzene / 2 h / Heating