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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.

SUBMITTER: Willand-Charnley R

PROVIDER: S-EPMC3365558 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Pyridine is an organocatalyst for the reductive ozonolysis of alkenes.

Willand-Charnley Rachel R Fisher Thomas J TJ Johnson Bradley M BM Dussault Patrick H PH

Organic letters 20120418 9

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. ...[more]

PMID: 22512349

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