Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2012

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.
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Dates and versions

hal-01002537 , version 1 (06-06-2014)

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Ghenia Bentabed-Ababsa, Samira Hamza-Reguig, Aïcha Derdour, Luis R. Domingo, José A. Sáez, et al.. Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes. Organic & Biomolecular Chemistry, 2012, 10, pp.8434. ⟨10.1039/C2OB26442K⟩. ⟨hal-01002537⟩
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