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PhI(OAc)(2) in the presence of OsO(4) (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with alpha-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO(4) (cat.), 2,6-lutidine, and PhI(OAc)(2).

An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4

An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)₂, NMO, and Catalytic OsO₄