Diastereoselective Synthesis and ESR Study of 4-PhenylDEPMPO Spin Traps

Autor:	and Antal Rockenbauer, Paul Tordo, Micael Hardy, Florence Chalier, Jean-Pierre Finet
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Spin trapping Organic Chemistry Electron Spin Resonance Spectroscopy Molecular Conformation Diastereomer Stereoisomerism Photochemistry Chemical synthesis Nitrone Adduct chemistry Pyrroles Stereoselectivity Cis–trans isomerism
Zdroj:	The Journal of Organic Chemistry. 70:2135-2142
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo0479516
Popis:	[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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::56ccd470053513ee1df55a4a59107ecd https://doi.org/10.1021/jo0479516 Zobrazit plný text záznamu