Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Authors

Rachel Willand-Charnley, University of Nebraska–Lincoln
Thomas J. Fisher, University of Nebraska–LincolnFollow
Bradley M. Johnson, University of Nebraska-LincolnFollow
Patrick Dussault, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

2012

Citation

Org Lett. 2012 May 4; 14(9): 2242–2245.

Comments

Copyright © 2012 American Chemical Society

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.