109460-99-3Relevant academic research and scientific papers
Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation
Morales, Sara,Guijarro, Fernando G.,Alonso, Inés,García Ruano, José Luis,Cid, M. Belén
, p. 84 - 91 (2016)
The formation of nitrones by direct condensation between equimolecular amounts of N-substituted hydroxylamine hydrochlorides and aromatic or aliphatic aldehydes is efficiently promoted by pyrrolidine in a matter of minutes under very mild conditions in almost quantitative yields after a simple filtration through a short pad of silica gel. According to theoretical, spectroscopic, and experimental studies, this success is due to the ability of pyrrolidine to liberate the hydrochloride of the hydroxylamine and catalyze the reaction via iminium activation ion. Moreover, a cooperative pyrrolidine/pyrrolidinium chloride effect facilitates several steps of the catalytic cycle through proton transfer without hampering the nucleophilicity of the hydroxylamine by protonation.
One-pot synthesis of functionalized nitrones from nitro compounds
Gautheron-Chapoulaud,Pandya,Cividino,Masson,Py,Valle?e
, p. 1281 - 1283 (2007/10/03)
The zinc-mediated reduction of nitroalkanes and nitroarenes in the presence of aldehydes is an efficient method to synthesize a wide range of nitrones. This method is mild enough to accommodate a variety of functional groups. It is particularly useful when the intermediate hydroxylamines are unstable and/or water-soluble. We used it to prepare several aromatic, aliphatic and highly functionalized sugar-derived nitrones.
