Fremy’s salt

salcomine; oxygen in N,N-dimethyl-formamide T=20°C; 2 h;

nitric acid; silver(l) oxide in 1,4-dioxane 0.25 h; Ambient temperature;

1: 2.) Zn/glacial acetic acid / 1.) 80 deg C, 8 h; 2.) 5 min 2: 75 percent / NaOH / methanol; H2O / Ambient temperature 3: 68 percent / H2 / 10percent Pd/C / ethanol / 5 h / 2068.6 Torr 4: 60 percent / decalin / 3 h / 160 °C 5: 50 percent / Ag2O, nitric acid / dioxane / 0.25 h / Ambient temperature View Scheme

1: 75 percent / NaOH / methanol; H2O / Ambient temperature 2: 68 percent / H2 / 10percent Pd/C / ethanol / 5 h / 2068.6 Torr 3: 60 percent / decalin / 3 h / 160 °C 4: 50 percent / Ag2O, nitric acid / dioxane / 0.25 h / Ambient temperature View Scheme

1: 68 percent / H2 / 10percent Pd/C / ethanol / 5 h / 2068.6 Torr 2: 60 percent / decalin / 3 h / 160 °C 3: 50 percent / Ag2O, nitric acid / dioxane / 0.25 h / Ambient temperature View Scheme

nitric acid; silver(l) oxide in 1,4-dioxane 0.25 h; Ambient temperature;

1: 60 percent / decalin / 3 h / 160 °C 2: 50 percent / Ag2O, nitric acid / dioxane / 0.25 h / Ambient temperature View Scheme

sulfuric acid in methanol 4 h; Heating;

1.1: 99 percent / K2CO3 / dimethylformamide / 4 h / 60 °C 2.1: 88 percent / mCPBA / CH2Cl2 / 1 h / 60 °C 3.1: 53 percent / AcOH / 3 h / 110 °C 4.1: 81 percent / pyridine / CH2Cl2 / 1 h / cooling 5.1: 90 percent / Et4NCl; PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 110 °C 6.1: Mg; 1,2-dibromoethane / tetrahydrofuran 6.2: tetrahydrofuran / 2 h / 20 °C 6.3: 87 percent / H2O2; KHCO3; KF / tetrahydrofuran; methanol / 3 h / 20 °C 7.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C 8.1: 85 percent / pyridinium chlorochromate; celite / CH2Cl2 / 10 h / 20 °C 9.1: 57 percent / NH2OH*HCl; AcONa / ethanol / 1 h / 85 °C 10.1: 49 percent / various solvent(s) / 1 h / 180 °C 11.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 12.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling 12.2: 64 percent / cyclohexane; diethyl ether; dioxane / 0.5 h / 20 °C 13.1: 85 percent / LiEt3BH / tetrahydrofuran / 0.17 h / cooling 14.1: 91 percent / H2 / Pd/C / ethanol / 2 h / 20 °C 15.1: 85 percent / salcomine; O2 / dimethylformamide / 2 h / 20 °C View Scheme