Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps.
[reaction: see text] 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 9with 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.
Hardy
Micaël
M
Laboratoire SREP, UMR 6517 CNRS et Universités Aix-Marseille 1, 2 et 3, Centre de Saint Jérôme, 13397 Marseille Cedex 20, France.
Chalier
Florence
F
Finet
Jean-Pierre
JP
Rockenbauer
Antal
A
Tordo
Paul
P
D004578:Electron Spin Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D011758:Pyrroles