Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation,ACS Catalysis

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Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation
ACS Catalysis ( IF 11.3 ) Pub Date : 2015-12-01 00:00:00 , DOI: 10.1021/acscatal.5b01726
Sara Morales ₁ , Fernando G. Guijarro ₁ , Inés Alonso ₁ , José Luis García Ruano ₁ , M. Belén Cid ₁

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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.

中文翻译：

吡咯烷和吡咯烷/吡咯烷鎓协同作用在硝基形成中的双重作用

在短时间内通过简单的硅胶垫过滤后，吡咯烷在非常温和的条件下，在几分钟左右的时间内，以相当定量的收率有效地促进了等摩尔量的N-取代的羟胺盐酸盐与芳香族或脂肪族醛之间直接缩合形成的硝酮。。根据理论，光谱和实验研究，该成功归因于吡咯烷释放羟胺盐酸盐并通过亚胺基活化离子催化反应的能力。此外，协同的吡咯烷/吡咯烷鎓氯化物作用通过质子转移促进了催化循环的几个步骤，而不会妨碍通过质子化作用的羟胺的亲核性。

更新日期：2015-12-01

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