bromine in chloroform

1: 99 percent / triethylamine / CH2Cl2 / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C 2: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 3: 97.7 percent / KOH / H2O; ethanol / 48 h 4: 75 percent / PPA / 2 h / 100 °C 5: NaBH4 / methanol / 16 h / Ambient temperature 6: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 7: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 8: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: dicyclohexyl-18-crown-6 ether / 1.) 0-5 deg C, 2.) 12 h, RT 2: borane-dimethyl sulfide 3: 99 percent / triethylamine / CH2Cl2 / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C 4: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 5: 97.7 percent / KOH / H2O; ethanol / 48 h 6: 75 percent / PPA / 2 h / 100 °C 7: NaBH4 / methanol / 16 h / Ambient temperature 8: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 9: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 10: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: borane-dimethyl sulfide 2: 99 percent / triethylamine / CH2Cl2 / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C 3: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 4: 97.7 percent / KOH / H2O; ethanol / 48 h 5: 75 percent / PPA / 2 h / 100 °C 6: NaBH4 / methanol / 16 h / Ambient temperature 7: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 8: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 9: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h 2: 97.7 percent / KOH / H2O; ethanol / 48 h 3: 75 percent / PPA / 2 h / 100 °C 4: NaBH4 / methanol / 16 h / Ambient temperature 5: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 6: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 7: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; acetic acid 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min;

1: NaBH4 / methanol / 16 h / Ambient temperature 2: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 3: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 4: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: 75 percent / PPA / 2 h / 100 °C 2: NaBH4 / methanol / 16 h / Ambient temperature 3: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 4: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 5: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 2: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme

1: 97.7 percent / KOH / H2O; ethanol / 48 h 2: 75 percent / PPA / 2 h / 100 °C 3: NaBH4 / methanol / 16 h / Ambient temperature 4: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h 5: N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / Heating 6: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min View Scheme