1: 1.) lithium diisopropylamide / 1.) 1.5h, -70 deg C to room temp., 2.) -70 deg C to room temp. 3: brown MnO2 / CHCl3 / 26 h / Heating 4: anhydrous Na2SO4, trifluoroacetic acid / CH2Cl2 / 0.92 h / Heating View Scheme

in hexane; dichloromethane 0.75 h; Heating;

1: 1.) lithium diisopropylamide / 1.) 1.5h, -70 deg C to room temp., 2.) -70 deg C to room temp. 3: brown MnO2 / CHCl3 / 26 h / Heating 4: anhydrous Na2SO4, trifluoroacetic acid / CH2Cl2 / 0.92 h / Heating View Scheme

2: brown MnO2 / CHCl3 / 26 h / Heating 3: anhydrous Na2SO4, trifluoroacetic acid / CH2Cl2 / 0.92 h / Heating View Scheme

1: 100 percent / N-bromosuccinimide / benzoyl peroxide / CCl4 / 2.5 h / Heating 2: 96 percent / H2O, sodium bicarbonate / tetrahydrofuran / 22.5 h 3: 99 percent / hexane; CH2Cl2 / 0.75 h / Heating View Scheme

1: 90 percent / activated MnO2 / CH2Cl2 / 16 h / Heating 2: 100 percent / N-bromosuccinimide / benzoyl peroxide / CCl4 / 2.5 h / Heating 3: 96 percent / H2O, sodium bicarbonate / tetrahydrofuran / 22.5 h 4: 99 percent / hexane; CH2Cl2 / 0.75 h / Heating View Scheme

1: 1.) phenyllithium / 1a) THF, -78 deg C, 15min; 1b) up to room temp.; 1c) room. temp., 45min; 2.) 2h, -78 deg C to room temp. 2: 90 percent / activated MnO2 / CH2Cl2 / 16 h / Heating 3: 100 percent / N-bromosuccinimide / benzoyl peroxide / CCl4 / 2.5 h / Heating 4: 96 percent / H2O, sodium bicarbonate / tetrahydrofuran / 22.5 h 5: 99 percent / hexane; CH2Cl2 / 0.75 h / Heating View Scheme

1: brown MnO2 / CHCl3 / 26 h / Heating 2: anhydrous Na2SO4, trifluoroacetic acid / CH2Cl2 / 0.92 h / Heating View Scheme

1: 1.) n-butyllithium / 1.) THF, 1h, -78 deg C to 0 deg C, 2.) -78 deg C to room temp. 2: 1.) phenyllithium / 1a) THF, -78 deg C, 15min; 1b) up to room temp.; 1c) room. temp., 45min; 2.) 2h, -78 deg C to room temp. 3: 90 percent / activated MnO2 / CH2Cl2 / 16 h / Heating 4: 100 percent / N-bromosuccinimide / benzoyl peroxide / CCl4 / 2.5 h / Heating 5: 96 percent / H2O, sodium bicarbonate / tetrahydrofuran / 22.5 h 6: 99 percent / hexane; CH2Cl2 / 0.75 h / Heating View Scheme

trifluoroacetic acid in dichloromethane 0.916667 h; Heating; Yield given;