6533b823fe1ef96bd127e253

RESEARCH PRODUCT

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

Ghenia Bentabed-ababsaJosé A. SáezEkhlass NassarFlorence MonginVincent DorcetSamira Hamza-reguigAicha DerdourLuis R. DomingoThierry Roisnel

subject

chemistry.chemical_classification010405 organic chemistryMethyl propiolate[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic Chemistrychemistry.chemical_elementRegioselectivity010402 general chemistryPhotochemistry01 natural sciencesBiochemistryChlorideMedicinal chemistryCycloaddition0104 chemical scienceschemistry.chemical_compoundchemistryPhenylacetyleneYlidemedicineReactivity (chemistry)Physical and Theoretical ChemistryIndiummedicine.drug

description

[EN] 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.

yearjournalcountryeditionlanguage
2012-09-27
10.1039/c2ob26442khttps://hdl.handle.net/10251/60355