Issue 24, 2010

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Aug 2010
Accepted
10 Sep 2010
First published
22 Oct 2010

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

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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