Me2AlSeMe in toluene 28 h; Reflux;

bis(2-pyridinyl)-disulfide; triphenylphosphine in toluene 28 h; Reflux;

1: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h 4: aq. KOH / 0.5 h / Heating View Scheme

1: 92.3 percent / diethyl ether / 2 h / Heating 2: p-toluenesulfonic acid / benzene / 16.5 h / Heating 3: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 4: 60 percent / phosphorus tribromide / diethyl ether / 3 h / Heating 5: 1.) lithium, ammonia, 2.) dimethylsulfoxide / 2.) THF, a) 2 h, b) 4 h 6: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 7: 76 percent / H2 / Pd/C / ethanol 8: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C View Scheme

1: 92.3 percent / diethyl ether / 2 h / Heating 2: p-toluenesulfonic acid / benzene / 16.5 h / Heating 3: H2 / 10percent palladium-on-carbon / ethanol / 5 h / Ambient temperature 4: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature View Scheme

sodium hydroxide; toluene-4-sulfonic acid 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h; Yield given. Multistep reaction;

1: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme