Oxonereg; in water; acetonitrile T=20°C; 1 h;

Oxonereg; in water; acetonitrile 5 h; Reflux;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; iron(II) oxalate dihydrate T=155 - 160°C; 0.5 h;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; iron(II) oxalate dihydrate T=155 - 160°C; 0.5 h;

Montmorillonite-K10; water T=80°C;

Oxonereg; in water; acetonitrile 5 h; Reflux;

in nitromethane; water T=50°C; 24 h;

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: 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 View Scheme

1: NaOEt / ethanol 2: (i) aq. KOH, EtOH, (ii) (decarboxylation) View Scheme