1: glacial acetic acid; concentrated sulfuric acid; fuming nitric acid 2: potassium permanganate View Scheme

perchloric acid; N-bromobenzamide; water in acetic acid T=19.9°C; ΔH*, ΔS*, other temp.; Thermodynamic dataKineticsRate constant;

sulfur trioxide pyridine complex; triethylamine in dichloromethane T=0°C; 1 h;

pyridine in ethyl acetate

toluene-4-sulfonic acid in acetone

bis(acetylacetonato) palladium; hydrogen; trimethylacetic anhydride; phenyldicyclohexylphosphine in tetrahydrofuran T=80°C; P=3750.38 Torr; 20 h; Inert atmosphere;

in acetone-water

manganese(IV) dioxide; acetic anhydride in tetrahydrofuran; toluene

1: 2) aq. NaOH, NaHCO3 / 1) THF, room temperature, 1 h, 2) THF, MeOH, room temperature 2: pyridinium chlorochromate / CH2Cl2; tetrahydrofuran / Ambient temperature View Scheme

1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / |Inert atmosphere 2: iron; ammonium chloride / water; ethanol / |Inert atmosphere; |Reflux 3: triethylamine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 4: sodium hydroxide / methanol / 2.5 h / 20 °C / |Inert atmosphere 5: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / |Inert atmosphere View Scheme