Alkene to Aldehyde

Common Conditions:

OsO₄ + NaIO₄

Osmium tetroxide (OsO4) forms the diol, then sodium periodate (NaIO4) oxidatively cleaves it. The solvent system is often THF/H2O or dioxane/H2O. The use of excess NaIO4 serves to regenerate OsO4, allowing the use of only a catalytic amount of toxic OsO4.^[1]

Examples

Reaction Map:

The reaction map is intended to provide insight into possible reactions one step before and after the title reaction. It also serves as an alternative way to navigate the website, and as a means of coming up with retrosynthetic ideas. Click on the reaction arrow to visit the page.