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Oxidative Cleavage of 1,2-Diols

Oxidative Cleavage of Vicinal Diols: Introduction

Starting materials

  • Vicinal diols (glycols)
  • Strong oxidizing agents, such as periodic acid (HIO4) or lead tetraacetate (Pb(OAc)4)

During the oxidative cleavage of vicinal diols, the oxidizing agents iodine(VII) and lead(IV) are reduced to iodine(V) and lead(II), respectively, and the C-C bond is being cleaved by oxidation of the alcohol groups. The reaction yields either two aldehyde groups, two keto groups or a mixture of both depending whether the OH groups in the diol are primary or secondary.


Movie: Glycol cleavage with periodate

Glycol cleavage with potassium periodate
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