T=450 - 460°C; 0.05 h;

1.1: potassium hydroxide / H2O / 5 h / Heating 1.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 2.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 3.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 4.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 5.1: ozone / methanol; CH2Cl2 / -78 °C 5.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 6.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 7.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 7.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 7.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 8.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 9.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 2.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 3.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4.1: ozone / methanol; CH2Cl2 / -78 °C 4.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 5.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 6.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 6.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 6.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 7.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 8.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 2.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3.1: ozone / methanol; CH2Cl2 / -78 °C 3.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 4.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 5.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 5.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 5.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 6.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 7.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 2.1: ozone / methanol; CH2Cl2 / -78 °C 2.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 3.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 4.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 4.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 4.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 5.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 6.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: ozone / methanol; CH2Cl2 / -78 °C 1.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 2.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 3.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 3.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 3.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 4.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 5.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 1.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 1.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 2.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 3.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: n-butyl lithium / hexane; tetrahydrofuran / 0.17 h / -78 °C 1.2: 99 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 99 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 3.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 4.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 4.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 5.1: potassium hydroxide / H2O / 5 h / Heating 5.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 6.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 7.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 8.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 9.1: ozone / methanol; CH2Cl2 / -78 °C 9.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 10.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 11.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 11.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 11.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 12.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 13.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: 92 percent / potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 2.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 2.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 3.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 4.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: 99 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 2.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 3.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 3.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 4.1: potassium hydroxide / H2O / 5 h / Heating 4.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 5.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 6.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 7.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 8.1: ozone / methanol; CH2Cl2 / -78 °C 8.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 9.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 10.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 10.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 10.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 11.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 12.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme