Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps

Micaël Hardy, Florence Chalier, Jean Pierre Finet, Antal 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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ASJC Scopus subject areas

  • Organic Chemistry

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