Reactions of alcohols with lead tetraacetate

The radical X is formed by homolysis of the X—R bond either thermally or photolytically. In the reactions of alcohols with lead tetraacetate evidence suggests that the X—R bond (X = 0, R = Pb(OAc)3) has ionic character. In this case the oxy radical is formed by a one electron transfer (thermally or photochemically induced) from oxygen to lead. 

The application of hypoiodite photolysis for remote functionalization has been mostly in the steroid field. There has been, however, a resurgence of appHcations in the field of spiroacetal-type compounds. The reaction was originally found in 1966 by Mihailovic and collaborators, who described remote functionalization by a thermal reaction of alcohols with lead tetraacetate. ... 

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