boron tribromide in dichloromethane 2.5 h; Ambient temperature;

1: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 2: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 3: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 4: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 5: 85 percent / BBr3 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

1: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 2: 85 percent / BBr3 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

1: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 2: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 3: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 4: 85 percent / BBr3 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

1: 24.4 percent / diethyl ether / 1 h / Heating 2: 93 percent / zinc amalgame, aq. HCl / toluene / 62 h / Heating 3: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 4: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 5: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 6: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 7: 85 percent / BBr3 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

palladium on activated charcoal; diphenylether T=270°C;

1: morpholine hydrochloride; ethanol / Behandeln der entstandenen Base mit Methyljodid in Aether und Erwaermen des Reaktionsprodukts mit der Natrium-Verbindung des 2-Methyl-acetessigsaeure-aethylesters in Aethanol und anschliessend mit Kalilauge 2: palladium/charcoal; diphenyl ether / 270 °C View Scheme

1: sulfur / 240 °C 2: aqueous HBr; acetic acid View Scheme

Reaktion ueber mehrere Stufen;

T=270°C;