Pyridine Is an Organocatalyst for the Reductive Ozonolysis of Alkenes
Organic Letters2012Vol. 14(9), pp. 2242–2245
Citations Over TimeTop 10% of 2012 papers
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.
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