sodium hexamethyldisilazane in tetrahydrofuran 1.) room temperature, 1 h, 2.) -90 deg C;

hydrogen; Lindlar's catalyst T=0°C; P=760 Torr;

sodium hexamethyldisilazane in tetrahydrofuran -100 deg C to RT;

1: 100 percent / NaBH4, H2 / Ni(OAc)2 / ethanol 2: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 3: 95 percent / acetonitrile / 15 h / 85 °C 4: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran 6: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 7: 92 percent / acetonitrile / 15 h / 85 °C 8: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

1: 98 percent / quinoline, H2 / Lindlar catalyst / hexane / 1 h / Ambient temperature 2: 96 percent / Ph3P, imidazole, I2 / tetrahydrofuran / -30 - 20 °C 3: 100 percent / calcium carbonate / acetonitrile / 72 h / 40 °C 4: 1.) n-BuLi / 1) THF, hexane, -45 deg C, 30 min; 2) THF, hexane, HMPA, -78 deg C, 30 min; 3) THF, hexane, HMPA, -78 deg C --> rt 5: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 6: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 7: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 8: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 9: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 10: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: fish oil With potassium hydroxide; water in methanol T=55°C; 1.5 h; 2: methanol With sulfuric acid in water T=20 - 55°C; 1.5 h; Product distribution / selectivity;

1: With potassium hydroxide; water in methanol T=55°C; 1.5 h; 2: methanol With sulfuric acid in water T=20 - 55°C; 1.5 h; Product distribution / selectivity;

1: (i) EtMgBr, THF, (ii) /BRN= 1840948/, CuCl 2: PBr3, Py / diethyl ether 3: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 4: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme

1: PBr3, Py / diethyl ether 2: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 3: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme

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