Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

R Willand-Charnley, TJ Fisher, BM Johnson…

Index: Willand-Charnley, Rachel; Fisher, Thomas J.; Johnson, Bradley M.; Dussault, Patrick H. Organic Letters, 2012 , vol. 14, # 9 p. 2242 - 2245

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Citation Number: 38

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.