Glycol Cleavage

Lead Tetraacetate Cleavage

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In this example lead tetraacetate is used cleave a carbon-carbon bond in a vicinal diol (glycol). This reaction is useful in the formation of ketones and aldehydes and involves a favourable five membered cyclic intermediate.

Click the structures and reaction black arrows in sequence to view the 3D models and animations respectively

A.-K. Schmidt and C. Stark, Synthesis (Stuttg)., 2014, 46, 3283–3308.