T=200°C;

tin(IV) chloride T=100°C; 2 h; Yields of byproduct given;

1: ethanol 2: aq. HCl View Scheme

1: 49 percent / AIBN / dioxane / 24 h / Heating 2: 1.) OsO4, N-methylmorpholine oxide, 2.) NaIO4 / 1.) Me2CO, H2O, , room temperature, 17 h, 2.) dioxane, H2O, room temperature, 40 h 3: BH3*Me2S / tetrahydrofuran / 3 h / 0 °C 4: 1.) PPh3, diisopropyl diazodicarboxylate, Zn(N3)2*2 pyridine, 2.) nBu3SnH, AIBN / 1.) toluene, room temperature, 24 h, 2.) benzene, reflux, 23 h View Scheme

1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; acetic acid

in N,N-dimethyl-formamide T=40°C; 4 h; Irradiation;

in dichloromethane; water T=40°C; 2 h; Irradiation;

in water; toluene T=40°C; 2 h; Irradiationvariation of solvent; MechanismProduct distribution;