Alkenes, cyclic, addition oxidative cleavage

Lead acetate azides, Pb(OAc)4 (N3)n, prepared in situ from lead tetraacetate and azidotrimethylsilane, react with alkenes to yield a variety of products, depending on the structure of the alkene 1,2-diazides. 1,2-acetoxy azides, a-azido ketones, allylic azides, and <5-oxo nitriles (by the oxidative cleavage of cyclohexene rings)97. The diazides and acetoxy azides are formed by preferential syn addition, but the diastereoselectivity (up to 3 1) is far from satisfactory with both acyclic and cyclic alkenes98,99. 

Oxidative cleavage of disulfides can be made by chemical and electrochemical means thus anodic oxidation at platinum or carbon electrodes of different kinds of disulfides in the presence of alkenes in acetonitrile affords products of acetamidosulfenylation with cyclic alkenes a high selectivity for trans addition is observed. The reaction may be formulated ... 

Additional examples of synthetic application of periodic acid as an oxidant include the oxidative iodination of aromatic compounds [1336-1341], iodohydrin formation by treatment of alkenes with periodic acid and sodium bisulfate [1342], oxidative cleavage of protecting groups (e.g., cyclic acetals, oxathioacetals and dithioacetals) [1315, 1343], conversion of ketone and aldehyde oximes into the corresponding carbonyl compounds [1344], oxidative cleavage of tetrahydrofuran-substituted alcohols to -y-lactones in the presence of catalytic PCC [1345] and direct synthesis of nitriles from alcohols or aldehydes using HsIOe/KI in aqueous ammonia [1346],... 

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