'Reductive ozonolysis' via a new fragmentation of carbonyl oxides

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

Research output: Contribution to journalArticle

30 Citations (Scopus)

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
StatePublished - Nov 13 2006

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Oxides
Amines
Dimethyl Sulfoxide
Alkenes
Aldehydes
1,2,4-trioxane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

'Reductive ozonolysis' via a new fragmentation of carbonyl oxides. / Schwartz, Chris; Raible, Joseph; Mott, Kyle; Dussault, Patrick H.

In: Tetrahedron, Vol. 62, No. 46, 13.11.2006, p. 10747-10752.

Research output: Contribution to journalArticle

Schwartz, Chris ; Raible, Joseph ; Mott, Kyle ; Dussault, Patrick H. / 'Reductive ozonolysis' via a new fragmentation of carbonyl oxides. In: Tetrahedron. 2006 ; Vol. 62, No. 46. pp. 10747-10752.
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