lithium perchlorate in acetonitrile T=85°C; Substitution; Ring cleavage; 3 h;

ethanol; platinum P=51485.6 Torr; Hydrogenation;

1.1: Mg / diethyl ether / 2 h / Heating 1.2: 93 percent / diethyl ether / 2 h / 20 °C 2.1: H2SO4 / acetic acid / 1 h / 60 °C 3.1: 96 percent / 4-phenylpyridine N-oxide / (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cycloh; exanediaminomanganese(III) / CH2Cl2 / 1.5 h / 0 - 5 °C / pH 11.3 4.1: 55 percent / LiClO4 / acetonitrile / 3 h / 85 °C View Scheme

1: 96 percent / 4-phenylpyridine N-oxide / (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cycloh; exanediaminomanganese(III) / CH2Cl2 / 1.5 h / 0 - 5 °C / pH 11.3 2: 55 percent / LiClO4 / acetonitrile / 3 h / 85 °C View Scheme

1: H2SO4 / acetic acid / 1 h / 60 °C 2: 96 percent / 4-phenylpyridine N-oxide / (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cycloh; exanediaminomanganese(III) / CH2Cl2 / 1.5 h / 0 - 5 °C / pH 11.3 3: 55 percent / LiClO4 / acetonitrile / 3 h / 85 °C View Scheme

benzene

benzene