hydrogen fluoride in acetonitrile T=-20°C; 48 h;

2: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 3: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 4: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 5: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 6: 100 percent 7: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 8: 20percent NaOH-H2O / 18.3 h / 16 °C 9: Jones reagent / 0.33 h / -30 °C 10: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

2: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 3: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 4: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 5: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 6: 100 percent 7: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 8: 20percent NaOH-H2O / 18.3 h / 16 °C 9: Jones reagent / 0.33 h / -30 °C 10: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 2: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 3: 100 percent 4: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 5: 20percent NaOH-H2O / 18.3 h / 16 °C 6: Jones reagent / 0.33 h / -30 °C 7: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 2: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 3: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 4: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 5: 100 percent 6: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 7: 20percent NaOH-H2O / 18.3 h / 16 °C 8: Jones reagent / 0.33 h / -30 °C 9: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 2: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 3: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 4: 100 percent 5: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 6: 20percent NaOH-H2O / 18.3 h / 16 °C 7: Jones reagent / 0.33 h / -30 °C 8: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

2: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 3: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 4: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 5: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 6: 100 percent 7: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 8: 20percent NaOH-H2O / 18.3 h / 16 °C 9: Jones reagent / 0.33 h / -30 °C 10: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 2: 100 percent 3: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 4: 20percent NaOH-H2O / 18.3 h / 16 °C 5: Jones reagent / 0.33 h / -30 °C 6: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

1: With chromium(VI) oxide in acetone T=4°C; 2: With hydrogen fluoride in tetrahydrofuran T=25°C; 4 h;

1: 87 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 1 h / Ambient temperature 2: 85 percent / HF / acetonitrile / 48 h / -20 °C View Scheme