potassium carbonate in acetone 1 h; Heating; Yield given. Yields of byproduct given;

1: aq. NaOH solution / Erwaermen des Reaktionsprodukts mit wss. Salzsaeure 2: copper; quinoline View Scheme

in pyridine Gibbs test; Mechanism;

1: 82 percent / aq. NH4OH; iodine; aq. KI / dioxane / 0.83 h / ice cooling 2: 86 percent / K2CO3 / dimethylformamide / 0.25 h / 80 °C 3: 92 percent / OsO4; 2-methyl-2-propanol; NaIO4 / dioxane; H2O / 2 h / 20 °C 4: 71 percent / tetra-n-butylammonium bromide; BF3-Et2O / CHCl3 / 0.5 h / Heating 5: 90 percent / Et3N; formic acid / Pd(AcO)2 / dimethylformamide / 11 h / 80 °C View Scheme

triphenylphosphine; trifluoroacetic acid in tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile

hydrogenchloride

1: K2CO3, KI / dimethylformamide / 70 - 80 °C 2: N,N-diethylaniline / Heating View Scheme

potassium carbonate; N,N-diethylaniline; potassium iodide 1.) DMF, 2.) reflux; Multistep reaction;

1: 66.7 percent / I2, aq.HIO4 / ethanol / 2 h / Ambient temperature 2: 51.7 percent / K2CO3, KI / acetone / 24 h / Heating 3: 74.6 percent / N,N-dimethylaniline / 12 h / Heating View Scheme