n-butyllithium in tetrahydrofuran; hexane T=-75°C; 0.0833333 h;

1: 89 percent / 2,2,6,6-tetramethylpiperidine; butyllithium; iodine / tetrahydrofuran; hexane / 2 h / -75 °C 2: 61 percent / diisopropylamine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 3: 83 percent / butyllithium / tetrahydrofuran; hexane / 0.08 h / -75 °C View Scheme

1: 61 percent / diisopropylamine; butyllithium / tetrahydrofuran; hexane / 2 h / -75 °C 2: 83 percent / butyllithium / tetrahydrofuran; hexane / 0.08 h / -75 °C View Scheme

potassium permanganate; tetrakis(triphenylphosphine) palladium(0) 1) dioxane, hexane, reflux, 2) H2O, reflux; Yield given. Multistep reaction;

2,2,6,6-tetramethylpiperidinyl-lithium in tetrahydrofuran T=-75°C; Product distribution; Further Variations:ReagentsSolvents;

1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 69 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

lithium aluminium tetrahydride; chloroformic acid ethyl ester; triethylamine 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min; Yield given. Multistep reaction;