1.1: 60 percent / K2OsO2(OH)4; hydroquinine 1,4-phthalazinediyl diether; aq. N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 49 h / 20 °C 2.1: BF3*OEt2 / CH2Cl2 / 1.83 h / 20 °C 3.1: acetyl bromide / CH2Cl2 / 2.5 h / 20 °C 4.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C 5.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C 5.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating 6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C 6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C 6.3: tetrahydrofuran; hexane / -85 - -20 °C 7.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr 8.1: 93 percent / 0.6 N aq. NaOH / 20 h / 4 °C 9.1: 79 percent / triethylamine; isopropenyl chloroformate / tetrahydrofuran / 1.25 h / 0 - 20 °C View Scheme

potassium carbonate

1.1: 60 percent / K2OsO2(OH)4; hydroquinine 1,4-phthalazinediyl diether; aq. N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 49 h / 20 °C 2.1: BF3*OEt2 / CH2Cl2 / 1.83 h / 20 °C 3.1: acetyl bromide / CH2Cl2 / 2.5 h / 20 °C 4.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C 5.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C 5.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating 6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C 6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C 6.3: tetrahydrofuran; hexane / -85 - -20 °C 7.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr 8.1: 93 percent / 0.6 N aq. NaOH / 20 h / 4 °C View Scheme

1: 59 percent / iPr2NH; BuLi; HMPA / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C 2: trityl fluoroborate / CDCl3 / 20 °C View Scheme

T=300 - 450°C; P=150012 Torr; 0.0166667 h; difference of activation energies; Product distributionThermodynamic data;

1: sodium hydride / tetrahydrofuran; dimethylsulfoxide 2: AlCl3 3: NaOMe 4: Ph2P(O)ONH2; NaH / dimethylformamide View Scheme

diisobutylaluminium hydride in dichloromethane T=-78°C; 1 h;

1: DBU / methanol 2: H2 / PtO2 / ethanol View Scheme

1: 1.)LDA, HMPA / 1.)THF 2: 1.)MCPBA, 2.)CF3COOH / 1.)CHCl3, 2 h, 2.)6 h View Scheme

copper(l) iodide in diethyl ether T=0°C;