lithium aluminium tetrahydride; lithium diisopropyl amide in tetrahydrofuran T=-30°C; Reduction;

lithium aluminium tetrahydride; lithium diisopropyl amide in tetrahydrofuran T=-30°C; Rearrangement; elimination, addition; 0.25 h;

1: 86 percent / KF / acetonitrile / 24 h / 22 °C 2: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C 3: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C 4: 81 percent / cerium(IV) ammonium nitrate, HNO3 / ethanol / 0.25 h / -42 °C 5: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C 6: pyridine / 1 h / 0 °C 7: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C 8: 4 N HCl / dioxane / 96 h / 22 °C 9: 554 mg / sodium acetate / 6.5 h / 50 °C 10: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 11: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 12: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 13: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 14: 49 percent / liquid ammonia, sodium / -78 °C View Scheme