tetrabutylammomium bromide; N-(dichloromethylene)-N,N-dimethylammonium chloride in dichloromethane T=0°C;

1: 93 percent / LiCl, CuCl2 / tetrahydrofuran / 24 h / 0 deg C to r.t. 2: 99 percent / HCl / methanol / 1 h / Heating View Scheme

1: 1.) lithium amide / 1.) ammonia, 2 h, 2.) THF, -33 deg C, 6 h 2: 62 percent / triphenyl phosphinem, carbon tetrachloride / 7 h / Heating 3: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) room temperature, 5 h 4: 0.280 g / sodium, liq. ammonia / 0.5 h 5: 78 percent / PTSA / methanol / 6 h / Ambient temperature 6: 80 percent / pyridinium fluorochromate / CH2Cl2 / 0.5 h View Scheme

1: (i) NaNH2, liq. NH3, (ii) aq. H2SO4, MeOH 2: H2, quinoline / Lindlar catalyst View Scheme

1.1: iodine; magnesium / tetrahydrofuran / 5.33 h / 20 °C / |Inert atmosphere; |Reflux 1.2: 12 h / 20 - 80 °C / |Ionic liquid 2.1: pyridinium p-toluenesulfonate / methanol / 50 °C View Scheme

1: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h 2: p-TsOH / methanol / 2 h / Heating 3: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C 4: 95 percent / pyridine / diethyl ether View Scheme

1.1: Mg / tetrahydrofuran 1.2: 40 percent / Li2CuCl4 / tetrahydrofuran 2.1: 90 percent / Ph3P; 2,4,4,6-tetrabromocyclohexa-2,5-dienone / CH2Cl2 / 20 °C View Scheme

1: 1) n-BuLi / 1) THF, HMPA, 0 deg C, 10 min, 2) rt, overnight 2: 93 percent / H2, quinoline / Pd/C/CaCO3 / hexane / 760 Torr 3: 77 percent / p-TsOH*H2O / methanol / 2 h / Ambient temperature 4: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 5: 1) LDA / 1) THF, -10 deg C, 10 min, 2) -78 deg C -> 25 deg C 6: 55 percent / CH2Cl2 / Ambient temperature View Scheme

1: hexamethylphosphoric acid triamide / 8 h / Ambient temperature 2: pyridinium p-toluenesulfonate / tetrahydrofuran; ethanol / 48 h / 55 - 60 °C View Scheme

toluene-4-sulfonic acid in chloroform