'Reductive ozonolysis' via a new fragmentation of carbonyl oxides

Chris Schwartz, Joseph Raible, Kyle Mott, Patrick H. Dussault

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Abstract

This account describes the development of methodologies for 'reductive' ozonolysis, the direct ozonolytic conversion of alkenes into carbonyl groups without the intermediacy of 1,2,4-trioxolanes (ozonides). Ozonolysis of alkenes in the presence of DMSO produces a mixture of aldehyde and ozonide. The combination of DMSO and Et3N results in improved yields of carbonyls but still leaves unacceptable levels of residual ozonides; similar results are obtained using secondary or tertiary amines in the absence of DMSO. The influence of amines is believed to result from conversion to the corresponding N-oxides; ozonolysis in the presence of amine N-oxides efficiently suppresses ozonide formation, generating high yields of aldehydes. The reactions with amine oxides are hypothesized to involve an unprecedented trapping of carbonyl oxides to generate a zwitterionic adduct, which fragments to produce the desired carbonyl group, an amine, and 1O2.

Original languageEnglish (US)
Pages (from-to)10747-10752
Number of pages6
JournalTetrahedron
Volume62
Issue number46
DOIs
Publication statusPublished - Nov 13 2006

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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