1.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 1.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 2.1: potassium hydroxide / H2O / 5 h / Heating 2.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 3.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 4.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 5.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 7.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 8.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 8.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 8.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 9.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 10.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 1.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 2.1: potassium hydroxide / H2O / 5 h / Heating 2.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 3.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 4.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 5.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 7.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 8.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 8.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 8.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 9.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 10.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

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

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