triethylamine in dichloromethane 1 h; Ambient temperature;

chlorine in tetrachloromethane 6 h; Irradiation;

1: Heating 3: 64 percent / diisobutylaluminium hydride / benzene / 0.25 h / 10 °C 4: 83 percent / Et3N / CH2Cl2 / 1 h / 0 °C 5: 16 percent / t-BuOK / tetrahydrofuran / 0.5 h / 20 °C 6: solid / 0.33 h / 15 - 20 °C / Irradiation; photolysis of benzene solution; photochemistry and rearrangements of bicyclo<3.1.0>hex-3-en-2-ones; solution photolysis, solution behavior; solid-state photolysis, crystal lattice behavior View Scheme

bromine; sodium hydrogencarbonate

1: 1.) CeCl3, 2.) NaBH4 / 1.) r.t., 5 min, 2.) r.t., 5 h 2: 80 percent / pyridine View Scheme

1: p-toluenesulfonic acid (PTSA) / 1.) reflux, 2.5 h, 2.) RT, 16 h 2: 1.) n-BuLi / 1.) THF, hexane, from 20 deg C to 0 deg C, 10 min, 2.) THF, hexane, 0.5 h 3: 98 percent / toluene / 8 h / Heating 4: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 5: 1 M aq. HCl / diethyl ether / 1 h 6: 1.) t-BuLi, 2.) dineopentylzinc 7: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 8: benzene; diethyl ether / 0.33 h 9: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 10: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 11: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 12: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 13: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 14: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 15: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

chlorine in dichloromethane T=20°C; Chlorination; 120 h;

N-bromosuccinmide in tetrachloromethane Irradiation;

1: Br2, aq. NaHCO3 View Scheme

1: H2 / Ni 2: TsOH View Scheme