Related Experiment Video
Updated: Jul 22, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide
Hakim Karoui1, Céline Nsanzumuhire, François Le Moigne
1Laboratoire 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.
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.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Thermal and Photochemical Electrocyclic Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
