title: Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes.
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.
authors.affiliation: Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences, Université d'Oran, BP 1524 El M'Naouer, 31000 Oran, Algeria. badri_sofi@yahoo.fr
authors.forename: Ghenia
authors.initials: G
authors.lastname: Bentabed-Ababsa
authors.forename: Samira
authors.initials: S
authors.lastname: Hamza-Reguig
authors.forename: Aïcha
authors.initials: A
authors.lastname: Derdour
authors.forename: Luis R
authors.initials: LR
authors.lastname: Domingo
authors.forename: José A
authors.initials: JA
authors.lastname: Sáez
authors.forename: Thierry
authors.initials: T
authors.lastname: Roisnel
authors.forename: Vincent
authors.initials: V
authors.lastname: Dorcet
authors.forename: Ekhlass
authors.initials: E
authors.lastname: Nassar
authors.forename: Florence
authors.initials: F
authors.lastname: Mongin