Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Rachel Willand-Charnley, Thomas J. Fisher, Bradley M. Johnson, Patrick H. Dussault

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2242-2245
Number of pages4
JournalOrganic Letters
Volume14
Issue number9
DOIs
StatePublished - May 4 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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