title: Pyridine is an organocatalyst for the reductive ozonolysis of alkenes.
abstract: Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, 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.
authors.affiliation: Department of Chemistry,  University of Nebraska-Lincoln , Lincoln, Nebraska 68588-0304, United States.
authors.forename: Rachel
authors.initials: R
authors.lastname: Willand-Charnley
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Fisher
authors.forename: Bradley M
authors.initials: BM
authors.lastname: Johnson
authors.forename: Patrick H
authors.initials: PH
authors.lastname: Dussault
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007659:Ketones; D011725:Pyridines; D010126:Ozone; C023666:pyridine