sodium hydroxide; sodium periodate in 1,4-dioxane T=0°C; 0.166667 h;

1: 82 percent / conc. H2SO4 / 2 h / Ambient temperature 2: 59 percent / pyridinium chlorochromate / CH2Cl2 / 16 h / Ambient temperature; or with pyridinium dichromate 3: 96 percent / aq. NaOH, aq. NaIO4 / dioxane / 0.17 h / 0 °C View Scheme

1: 59 percent / pyridinium chlorochromate / CH2Cl2 / 16 h / Ambient temperature; or with pyridinium dichromate 2: 96 percent / aq. NaOH, aq. NaIO4 / dioxane / 0.17 h / 0 °C View Scheme

pyridinium p-toluenesulfonate 1.5 h; Heating;

pyridinium p-toluenesulfonate T=60°C; 2.5 h; influence of temperature, reaction time; Product distribution;

1: pyridinium p-toluenesulfonate / 12 h / 60 °C 2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C (3 h), -> room temp. (1 h) View Scheme