alexa State of the Art of the Bonding Changes along the Diels
ISSN: 2161-0401

Organic Chemistry: Current Research
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Research Article

State of the Art of the Bonding Changes along the Diels-Alder Reaction between Butadiene and Ethylene: Refuting the Pericyclic Mechanism

Domingo LR*
Departamento de Química Orgánica, Universidad de Valencia, Dr. Moliner 50, E-46100 Burjassot, Valencia, Spain
Corresponding Author : Domingo LR
Departamento de Química Orgánica
Universidad de Valencia, Dr. Moliner 50
E-46100 Burjassot, Valencia, Spain
E-mail: [email protected];
web: www.luisrdomingo.com
Received September 05, 2013; Accepted October 05, 2013; Published October 10, 2013
Citation: Domingo LR (2013) State of the Art of the Bonding Changes along the Diels-Alder Reaction between Butadiene and Ethylene: Refuting the Pericyclic Mechanism. Organic Chem Curr Res 2:120. doi:10.4172/2161-0401.1000120
Copyright: © 2013 Domingo LR. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
 

Abstract

Bonding changes along the Diels-Alder reaction between butadiene 1 and ethylene 2 and related non-polar Diels- Alder reactions have been analysed using the Bonding Evolution Theory (BET). The Electron Localization Function (ELF) analysis of these synchronous single bond-formation processes indicates that C-C bond formation takes place by the C-to-C coupling of two pseudoradical centers formed along the reaction. The present study permits the establishment of two significant findings: i) the breaking of the C=C double bonds in butadiene 1 and ethylene 2 and the formation of the new C-C single bonds in cycloadduct are non-concerted due to the changed in electron density required for the formation of the pseudoradical centers, and ii) the symmetric changes in electron density along these cycloadditions do not have a cyclic movement. These behaviours, which are opposite to the “concerted and close curve bonding changes” proposed by R. B. Woodward and R. Hoffmann for pericyclic reactions, allow refuting this mechanism for Diels-Alder reactions.

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