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Pyridine Is an Organocatalyst for the Reductive Ozonolysis of Alkenes

Rachel Willand-Charnley, Thomas J. Fisher, Bradley M. Johnson and Patrick H. Dussault*

*Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, United States, Email: pdussault1unl.edu

R. Willand-Charnley, T. J. Fisher, B. M. Johnson, P. H. Dussault, Org. Lett., 2012, 14, 2242-2245.

DOI: 10.1021/ol300617r (free Supporting Information)


Abstract

Ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

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proposed mechanism



Ozonolysis in Solvent/Water Mixtures: Direct Conversion of Alkenes to Aldehydes and Ketones

C. E. Schiaffo, P. H. Dussault, J. Org. Chem., 2008, 73, 4688-4690.


Key Words

Ozonolysis, Organocatalysis


ID: J54-Y2012-1300