Issue 24, 2010
From the journal:

Organic & Biomolecular Chemistry

Understanding the mechanism of non-polar Diels–Alder reactions. A comparative ELF analysis of concerted and stepwise diradical mechanisms†

Luis R. Domingo,*a   Eduardo Chamorrob  and  Patricia Pérezb  

* Corresponding authors

a Universidad de Valencia, Departamento de Química Orgánica, Dr Moliner 50, Valencia, Spain
E-mail: domingo@utopia.uv.es
Fax: (+34) 96 354 4328

b Universidad Andres Bello, Departamento de Ciencias Químicas, Facultad de Ecología y Recursos Naturales, Laboratorio de Química Teórica, Av. República 275, Santiago, Chile

Abstract

The electron-reorganization along the concerted and stepwise pathways associated with the non-polar Diels–Alder reaction between cyclopentadiene (Cp, 1) and ethylene (2) has been studied using the topological analysis of the electron localization function (ELF) at the B3LYP/6-31G(d) level of theory. ELF results for the concerted mechanism stresses that the electron-reorganization demanded on the diene and ethylene reagents to reach two pseudo-diradical structures is responsible for the high activation energy. A comparative ELF analysis of some relevant points of the non-polar Diels–Alder reaction between Cp and styrene (10) suggests that these concerted mechanisms do not have a pericyclic electron-reorganization.

Graphical abstract: Understanding the mechanism of non-polar Diels–Alder reactions. A comparative ELF analysis of concerted and stepwise diradical mechanisms

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Article information

DOI
https://doi.org/10.1039/C0OB00563K
Article type
Paper
Submitted
10 Aug 2010
Accepted
10 Sep 2010
First published
22 Oct 2010

Org. Biomol. Chem., 2010,8, 5495-5504

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Understanding the mechanism of non-polar Diels–Alder reactions. A comparative ELF analysis of concerted and stepwise diradical mechanisms

L. R. Domingo, E. Chamorro and P. Pérez, Org. Biomol. Chem., 2010, 8, 5495 DOI: 10.1039/C0OB00563K

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