N-benzyl-trimethylammonium hydroxide in dimethyl sulfoxide

chloranil; xylene

1: N2H4+H2O; KOH; ethylene glycol 2: tetrachloro<1,4>benzoquinone; xylene View Scheme

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 1.5 h; HeatingIrradiation;

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h View Scheme

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h 3: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h View Scheme

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h 3: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 4: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h View Scheme

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h 3: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 4: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 5: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature View Scheme

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h 3: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 4: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 5: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: 1.8 g / oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 7: AlCl3 / CS2 / 1.) 0 deg C , 1h, 2.) reflux , 30 min 8: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature 9: 72 percent / HCl / acetic acid / 1 h / 90 °C View Scheme

1: AlCl3 / nitrobenzene / 6 h / Ambient temperature 2: Zn(Hg), HCl / acetic acid; toluene / 3 h / Heating 3: 1.) (COCl)2, 2.) AlCl3 / 1.) CH2Cl2, RT, 1 h, 2.) CS2, reflux, 30 min 4: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 5: PTSA / benzene / 0.5 h / Heating 6: DDQ / benzene / 0.17 h / Heating View Scheme