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Karoui H, Nsanzumuhire C, Le Moigne F, et al. Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide. J Org Chem. 1999;64(5):1471-1477doi: 10.1021/jo981875n.
Karoui, H., Nsanzumuhire, C., Le Moigne, F., & Tordo, P. (1999). Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide. The Journal of organic chemistry, 64(5), 1471-1477. https://doi.org/10.1021/jo981875n
Karoui, Hakim, et al. "Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide." The Journal of organic chemistry vol. 64,5 (1999): 1471-1477. doi: https://doi.org/10.1021/jo981875n
Karoui H, Nsanzumuhire C, Le Moigne F, Tordo P. Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide. J Org Chem. 1999 Mar 05;64(5):1471-1477. doi: 10.1021/jo981875n. PMID: 11674206.
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J Org Chem. 1999 Mar 05;64(5):1471-1477. doi: 10.1021/jo981875n.

Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide.

The Journal of organic chemistry

Hakim Karoui, Céline Nsanzumuhire, François Le Moigne, Paul Tordo

Affiliations

  1. Laboratoire Structure et Réactivité des Espèces Paramagnétiques, case 521, CNRS UMR 6517 "Chimie, Biologie et Radicaux Libres", Universités d'Aix-Marseille I et III, Centre de Saint Jérôme, Av. Escadrille Normandie Niemen, 13397 Marseille Cedex 20, France.

PMID: 11674206 DOI: 10.1021/jo981875n

Abstract

Recently, the synthesis of a new phosphorylated nitrone, 2-(diethoxyphosphoryl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide (DEPMPO) (2) was described. The presence of the phosphorylated group strongly stabilized the DEPMPO-superoxide spin adduct. To understand the role of the diethoxyphosphoryl group in this stabilization, a new phosphorylated nitrone, 2-(diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-oxide (DEPPPO) (7), was prepared through a four-step synthetic pathway, and its ability to trap free radicals was investigated. Data obtained from spin trapping experiments of a wide variety of free radicals generated in situ showed the formation of two diastereoisomers spin adducts with different phosphorus and hydrogen coupling constants. Superoxide trapping by DEPPPO gave a persistent nitroxide spin adduct, and its half-time life was measured and compared to that of the DEPMPO analogue.

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