Issue 42, 2012
From the journal:

Organic & Biomolecular Chemistry

Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes†

Ghenia Bentabed-Ababsa,*ab   Samira Hamza-Reguig,a   Aïcha Derdour,a   Luis R. Domingo,*c   José A. Sáez,c   Thierry Roisnel,d   Vincent Dorcet,d   Ekhlass Nassare  and  Florence Mongin*b  

* Corresponding authors

a Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences, Université d'Oran, BP 1524 El M'Naouer, 31000 Oran, Algeria
E-mail: badri_sofi@yahoo.fr
Fax: +213-04158-2540
Tel: +213-79175-8768

b Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes Cedex, France
E-mail: florence.mongin@univ-rennes1.fr
Fax: +33-2-2323-6955
Tel: +33-2-2323-6931

c Departamento de Química Orgánica, Universidad de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain
E-mail: domingo@utopia.uv.es
Fax: +34-9-6354-4328
Tel: +34-9-6354-3106

d Centre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Bâtiment 10B, Campus Scientifique de Beaulieu, 35042 Rennes Cedex, France

e Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Asma Fahmy Street, Heleopolis (El-Margany), Cairo, Egypt

Abstract

The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoretically investigated using DFT methods in order to explain the reactivity and regioselectivity observed.

Graphical abstract: Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes

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Article information

DOI
https://doi.org/10.1039/C2OB26442K
Article type
Paper
Submitted
24 Jul 2012
Accepted
11 Sep 2012
First published
12 Sep 2012

Org. Biomol. Chem., 2012,10, 8434-8444

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Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes

G. Bentabed-Ababsa, S. Hamza-Reguig, A. Derdour, L. R. Domingo, J. A. Sáez, T. Roisnel, V. Dorcet, E. Nassar and F. Mongin, Org. Biomol. Chem., 2012, 10, 8434 DOI: 10.1039/C2OB26442K

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