Lead tetraacetate with carboxylate ions

One-electron oxidation of carboxylate ions generates acyloxy radicals, which undergo decarboxylation. Such electron-transfer reactions can be effected by strong one-electron oxidants, such as Mn(HI), Ag(II), Ce(IV), and Pb(IV) These metal ions are also capable of oxidizing the radical intermediate, so the products are those expected from carbocations. The oxidative decarboxylation by Pb(IV) in the presence of halide salts leads to alkyl halides. For example, oxidation of pentanoic acid with lead tetraacetate in the presence of lithium chloride gives 1-chlorobutane in 71% yield ... 

Some oxidants are rather specific in their action and tend to bring about a preferred type of oxidation. A few such oxidants are periodate ion, lead tetraacetate, bismuthate ion, or trivalent silver, which oxidize adjacent secondary alcohol groups with chain cleavage to dialdehydes, and nitrogen dioxide, which preferentially oxidizes primary alcohol groups to carboxyl groups. 

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