thionyl chloride; trifluoroacetic anhydride 24 h; Ambient temperature; Further byproducts given;

trifluoroacetic anhydride 24 h; Ambient temperature; Further byproducts given;

air; trifluoroacetic anhydride 64 h; Ambient temperatureother times, or with 18O2, or without oxygen; Product distributionMechanism;

1: sulfuric acid / 24 h / |Reflux; |Inert atmosphere 2: [Ir(cod)Py(3)]+[BArF]-; hydrogen / dichloromethane / 1500.15 Torr / |Inert atmosphere 3: lithium aluminium tetrahydride / |Inert atmosphere View Scheme

1: PCl3 3: MCPBA / CH2Cl2 / 12 h / 35 °C 4: 76 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Bis(2-hydroxyethyl)lauramide 1.) THF, 0 deg C, 30 min, 2.) THF, rt, 16 h; Yield givenMultistep reaction. Yields of byproduct given;

n-butyllithium in tetrahydrofuran other reagent; Product distribution;

(i) Br2, (ii) (dehydrobromination); Multistep reaction;

in 1,2-dichloro-ethane T=80°C; 1 h;

1.1: thionyl chloride 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.75 h / -78 - 0 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 3.2: 6 h / -50 °C 4.1: lithium borohydride / tetrahydrofuran / 0 °C 5.1: 1H-imidazole / dichloromethane / 20 °C 6.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -40 °C 7.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 20 °C / |Inert atmosphere 8.1: N,N,N',N,-tetramethylethylenediamine; anhydrous iron chloride / tetrahydrofuran / 0.5 h / 0 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C 11.1: tetrahydrofuran / 2.25 h / 0 - 20 °C 12.1: pyridine / 20 °C 13.1: potassium tert-butylate / dimethyl sulfoxide / 5 h / 20 °C 14.1: methyl-magnesium iodide / diethyl ether / 0.17 h / 180 °C / |Inert atmosphere View Scheme