1: 1.) sec-BuLi, HMPA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT, 2 h 2: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

Multistep reaction;

1: 1.) t-butyllithium / 1.) HMPA 2: HCl / acetone View Scheme

potassium methanolate 1.) methanol, 5 deg C, 10 min, 2.) reflux, 3.5 h; Yield given. Multistep reaction;

1: 3-ethoxy-2-cyclohexen-1-one With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h; 2: 4-pentenyl iodide in tetrahydrofuran T=-78 - 23°C; 5 h;

1: 1) n-BuLi, N-isopropylcyclohexylamine / 1) THF, -70 deg C, 1 h, 2) THF, HMPA, r.t., overnight 2: 20percent aq. NaOH / methanol / 2 h / Heating 3: 1) diphenylphosphorazidate, Et3N, 2) 15percent HCl, AcOH / 1) benzene, a) 1 h, b) r.t., 1 h, c) reflux, 3 h, 2) r.t., overnight 4: 60 percent / SO2Cl2, Et3N / diethyl ether / a) -70 deg C, 2 h, b) -20 deg C, overnight 5: 1) NaH, 2) tert-butyl hypochlorite / 1) hexane, r.t., 3 h, 2) hexane, r.t., overnight 6: 43 percent / diethyl ether / 6 h / 23 °C / Irradiation; variation of concentration; addition of Ph2PH; addition of Mg-powder, activated by various methods View Scheme

1: 1) n-BuLi, N-isopropylcyclohexylamine / 1) THF, -70 deg C, 1 h, 2) THF, HMPA, r.t., overnight 2: 20percent aq. NaOH / methanol / 2 h / Heating 3: 1) diphenylphosphorazidate, Et3N, 2) 15percent HCl, AcOH / 1) benzene, a) 1 h, b) r.t., 1 h, c) reflux, 3 h, 2) r.t., overnight 4: 60 percent / SO2Cl2, Et3N / diethyl ether / a) -70 deg C, 2 h, b) -20 deg C, overnight 5: 1) NaH, 2) tert-butyl hypochlorite / 1) hexane, r.t., 3 h, 2) hexane, r.t., overnight 6: 26 percent / diethyl ether / 6 h / 23 °C / Irradiation; variation of concentration; addition of Ph2PH; addition of Mg-powder, activated by various methods View Scheme

1: 1) n-BuLi, N-isopropylcyclohexylamine / 1) THF, -70 deg C, 1 h, 2) THF, HMPA, r.t., overnight 2: 20percent aq. NaOH / methanol / 2 h / Heating View Scheme

bis-triphenylphosphine-palladium(II) chloride; potassium carbonate in water; benzene T=20°C; P=34202.3 Torr; 16 h; AutoclaveIrradiation;

decacarbonyldimanganese (2) in benzene P=57000 Torr; 16 h; Photolysis;