Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps

Micaël Hardy, Florence Chalier, Jean Pierre Finet, A. Rockenbauer, Paul Tordo

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Abstract

(Chemical Equation Presented) The cis and trans diastereoisomers of 5-(diethoxyphosphoryl)-5-methyl-4-phenylpyrroline N-oxide (4-PhDEPMPOt 8 and 4-PhDEPMPOc 9) were prepared stereoselectively and used as spin traps for hydroxyl and superoxide radicals. The spin adduct formed by reaction of the cis stereoisomer 9 with superoxide radical anion exhibited an 8-line ESR spectrum, showing only a reduced alternating line width phenomenon. This spectrum is simpler than the 12-line spectrum of DEPMPO-OOH, which exhibits a strong alternating line width phenomenon. The half-life times of the 4-PhDEPMPOc-OOH and DEPMPO-OOH adducts were of the same order: 14.5 and 15.5 min, respectively.

Original languageEnglish
Pages (from-to)2135-2142
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number6
DOIs
Publication statusPublished - Mar 18 2005

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Superoxides
Linewidth
Paramagnetic resonance
Stereoisomerism
Hydroxyl Radical
Oxides
Anions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps. / Hardy, Micaël; Chalier, Florence; Finet, Jean Pierre; Rockenbauer, A.; Tordo, Paul.

In: Journal of Organic Chemistry, Vol. 70, No. 6, 18.03.2005, p. 2135-2142.

Research output: Contribution to journalArticle

Hardy, Micaël ; Chalier, Florence ; Finet, Jean Pierre ; Rockenbauer, A. ; Tordo, Paul. / Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 6. pp. 2135-2142.
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