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Título: | Cycloadditions: Concerted vs diradical stepwise mechanisms. The case of nitrones dimerization |
Autor: | Roca-López, David CSIC ORCID; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID | Fecha de publicación: | 2013 | Citación: | 15th JCF-Frühjahrssymposium (2013) | Resumen: | The [3+2] cycloaddition reaction of olefinic dipolarophiles with 1,3-dipoles, such as nitrile oxides or nitrones, is one of the best known and most widely used method for constructing five-membered heterocycles. Nitrile oxides easily dimerize to furoxans, and the mechanism of the process has been already elucidated. However, the analogous process with nitrones is a rarely reported event witnessed previously in few cases for cyclic nitrones. Recently, the cyclodimerization of several six-membered nitrones was investigated,[3] but only configurational and conformational features of the dimers were studied, without shedding light on the mechanism, which remains in controversy. Especially, because the apparent dimerization process consists in an unfavored thermal [4π+4π] cycloadition reaction, and no information exists to date about the electronic and steric effects on dimerization of nitrones and the nature of the transition states for such a process. In this work, we report DFT studies (both open- and closed-shell) on the dimerization of nitrones, first on a simple model and after on the 2,3,4,5-tetrahydropyridine-1-oxide, using up to the PCM(dichloromethane)/M06–2X/cc–pVTZ level of calculation. | Descripción: | Trabajo presentado al 15th JCF Frühjahrssymposium (Congreso de Jóvenes Investigadores de la Sociedad Alemana de Química) celebrado en Berlín (Alemania) del 6 al 9 de marzo de 2013. | URI: | http://hdl.handle.net/10261/112086 |
Aparece en las colecciones: | (ISQCH) Comunicaciones congresos |
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