255052-05-2Relevant articles and documents
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 (2016/01/12)
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.
Rapid, efficient, and room temperature synthesis of nitrones in excellent yields over MgO under solvent-free conditions
Valizadeh, Hassan,Dinparast, Leila
experimental part, p. 177 - 181 (2009/10/04)
A large variety of C-aryl and C-alkyl nitrones were synthesized within 0.5-15 min via the condensation of aldehydes with N-(methyl, phenyl, or t-butyl)hydroxylamines over MgO by hand-grinding with an agate mortar. These reactions were investigated under d
