Jump to main content
Jump to site search

Issue 24, 2010
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Aug 2010, accepted on 10 Sep 2010 and first published on 22 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00563K
Citation: Org. Biomol. Chem., 2010,8, 5495-5504
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements