1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 3: 98 percent Turnov. / lithium aluminum hydride / diethyl ether / 0.17 h View Scheme

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 85 percent / 18-crown-6 ether / acetonitrile / 288 h / Ambient temperature 3: 2.) hydrochloric acid / !:) ethyl ether, THF, reflux, 2.5 h, 2.) reflux, 3 h 4: 69 percent / ethanol / 2 h / Heating 5: 21 percent / tert-butyllithium / pentane; tetrahydrofuran / 1.) -78 deg C, 24 h, 2.) room temperature 6: 85 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / 0 °C 7: 93 percent / boron trifluoride etherate / diethyl ether / 3 h / Ambient temperature View Scheme

silver(I) acetate in acetic acid T=75°C; 39 h;

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: methanol / 50 h / Heating View Scheme

in acetic acid T=75°C; 39 h;

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 1.) cuprous iodide / 1.) ethyl ether, 2.) 25 deg C, 30 h 3: 80 percent / 456 °C / 0.1 Torr View Scheme

in acetic acid T=75°C; 16 h;

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 97 percent / xylene / 72 h / Heating 3: 1.) tert-butyllithium / 1.) pentane, 2.) reflux, 2 h 4: 550 °C / 0.1 Torr View Scheme

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 85 percent / 18-crown-6 ether / acetonitrile / 288 h / Ambient temperature 3: 2.) hydrochloric acid / !:) ethyl ether, THF, reflux, 2.5 h, 2.) reflux, 3 h 4: 69 percent / ethanol / 2 h / Heating 5: 21 percent / tert-butyllithium / pentane; tetrahydrofuran / 1.) -78 deg C, 24 h, 2.) room temperature 6: 44 percent / 550 °C / 0.1 Torr View Scheme

1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 83 percent Turnov. / sodium methoxide / ethanol / 48 h / Heating 3: 93 percent / N-chlorosuccinimide / CCl4 / 12 h / Heating 4: 12 percent / aq sodium carbonate / 48 h / 20 - 25 °C / further reagents 5: 69 percent / Ambient temperature View Scheme