sodium dihydrogenphosphate; Fremy’s salt; Aliquatreg; 336 in dichloromethane; water Fremy's salt oxidation;

silver carbonate in benzene 2 h;

1: 65 percent / Et3N, Ph3P / Pd(OAc)2 / 12 h / 80 °C 2: 95 percent / H2 / Pd/C / ethanol 3: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 4: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 5: 94 percent / 48percent HBr / ethanol / 1 h 6: 94 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 82 percent / K2CO3 / acetone / 10 h / Heating 2: 65 percent / Et3N, Ph3P / Pd(OAc)2 / 12 h / 80 °C 3: 95 percent / H2 / Pd/C / ethanol 4: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 5: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 6: 94 percent / 48percent HBr / ethanol / 1 h 7: 94 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 65 percent / Et3N, Ph3P / Pd(OAc)2 / 12 h / 80 °C 2: 95 percent / H2 / Pd/C / ethanol 3: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 4: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 5: 94 percent / 48percent HBr / ethanol / 1 h 6: 94 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 95 percent / H2 / Pd/C / ethanol 2: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 3: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 4: 94 percent / 48percent HBr / ethanol / 1 h 5: 94 percent / Ag2CO3 / benzene / 2 h View Scheme

1: 98 percent / CuI; Pd(PPh3) / various solvent(s) / 0.5 h / 20 °C 2: 99.8 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethanol / 1 h / 0 - 20 °C 3: 97 percent / 4-methylmorpholine-N-oxide; 4 Angstroem m. s.; TPAP / CH2Cl2 / 0.17 h 4: 85 percent / potassium t-butoxide / dioxane / 1 h / 20 °C 5: 99.8 percent / 2M HCl / propan-2-ol; tetrahydrofuran / 1 h / 20 °C 6: 87 percent / potassium nitrosodisulfonate (Fremy's salt); NaH2PO4*H2O; Aliquat 336 / H2O; CH2Cl2 View Scheme

1: 98 percent / CuI; Pd(PPh3) / various solvent(s) / 0.5 h / 20 °C 2: 99.8 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethanol / 1 h / 0 - 20 °C 3: 97 percent / 4-methylmorpholine-N-oxide; 4 Angstroem m. s.; TPAP / CH2Cl2 / 0.17 h 4: 85 percent / potassium t-butoxide / dioxane / 1 h / 20 °C 5: 99.8 percent / 2M HCl / propan-2-ol; tetrahydrofuran / 1 h / 20 °C 6: 87 percent / potassium nitrosodisulfonate (Fremy's salt); NaH2PO4*H2O; Aliquat 336 / H2O; CH2Cl2 View Scheme

1: 99.8 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethanol / 1 h / 0 - 20 °C 2: 97 percent / 4-methylmorpholine-N-oxide; 4 Angstroem m. s.; TPAP / CH2Cl2 / 0.17 h 3: 85 percent / potassium t-butoxide / dioxane / 1 h / 20 °C 4: 99.8 percent / 2M HCl / propan-2-ol; tetrahydrofuran / 1 h / 20 °C 5: 87 percent / potassium nitrosodisulfonate (Fremy's salt); NaH2PO4*H2O; Aliquat 336 / H2O; CH2Cl2 View Scheme

1: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 2: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 3: 94 percent / 48percent HBr / ethanol / 1 h 4: 94 percent / Ag2CO3 / benzene / 2 h View Scheme