T=375°C; 0.000277778 h; various solvents and free radical inhibitors; Product distribution;

iodine in benzene 0.333333 h; Heating;

1: NaBH4 / CeCl3 / methanol 2: ZnCl2 / benzene / 20 h / Heating View Scheme

1: 78 percent Chromat. / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating 3: 61 percent / potassium tert-butoxide / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 4: 1.) NaBH4, cerium (III) chloride hydrate, 2.) triethylamine, 2,4-dinitrobenzenesulfenyl chloride / 1.) methanol, 10 min, 2.) a) dichloromethane, -35 deg c, 0.5 h, b) RT, 3 h View Scheme

1: 1.) lithium aluminium hydride, 2.) pyridine, p-toluenesulfonyl chloride / 1.) ether, 45 min, 2.) RT, 4 d 2: 78 percent Chromat. / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating 4: 61 percent / potassium tert-butoxide / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 5: 1.) NaBH4, cerium (III) chloride hydrate, 2.) triethylamine, 2,4-dinitrobenzenesulfenyl chloride / 1.) methanol, 10 min, 2.) a) dichloromethane, -35 deg c, 0.5 h, b) RT, 3 h View Scheme

2: 61 percent / potassium tert-butoxide / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 3: 1.) NaBH4, cerium (III) chloride hydrate, 2.) triethylamine, 2,4-dinitrobenzenesulfenyl chloride / 1.) methanol, 10 min, 2.) a) dichloromethane, -35 deg c, 0.5 h, b) RT, 3 h View Scheme

1: 1.) t-BuLi / 1.) hexane, THF, from -50 deg c to -20 deg C, 2.) THF, hexane, from -20 deg C to RT 2: 1.) lithium aluminium hydride, 2.) pyridine, p-toluenesulfonyl chloride / 1.) ether, 45 min, 2.) RT, 4 d 3: 78 percent Chromat. / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating 5: 61 percent / potassium tert-butoxide / hexamethylphosphoric acid triamide / 2 h / Ambient temperature 6: 1.) NaBH4, cerium (III) chloride hydrate, 2.) triethylamine, 2,4-dinitrobenzenesulfenyl chloride / 1.) methanol, 10 min, 2.) a) dichloromethane, -35 deg c, 0.5 h, b) RT, 3 h View Scheme

sodium tetrahydroborate; cerium(III) chloride; 2,4-dinitrobenzene-sulfenyl chloride; triethylamine 1.) methanol, 10 min, 2.) a) dichloromethane, -35 deg c, 0.5 h, b) RT, 3 h; Yield given. Multistep reaction;