Osmium Tetroxide-Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis

Benjamin R. Travis, Radha S. Narayan and Babak Borhan*

*Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, Email: babakchemistry.msu.edu

B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc., 2002, 124, 3824-3825.

DOI: 10.1021/ja017295g

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Abstract

The OsO₄-catalyzed direct oxidation of olefins via the carbon-carbon cleavage of an osmate ester by the action of oxone allows the preparation of ketones or carboxylic acids in high yields. This method should be applicable as an alternative to ozonolysis.

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proposed mechanism

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Key Words

Osmium Tetroxide, Oxone, Ozonolysis, Oxidative Cleavage of Alkenes (Products: Ketones, Carboxylic Acids)

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ID: J48-Y2002-1090