0000000000524471

AUTHOR

Samira Hamza-reguig

showing 4 related works from this author

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

2012

[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.

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
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A combined experimental and theoretical study of the thermal [3+2] cycloaddition of carbonyl ylides with activated alkenes

2018

International audience; 4-Benzoyl-3,5-diaryltetrahydrofuran-2,2-dicarbonitriles were first synthesized from 2,2-dicyano-3-aryloxiranes and chalcones at toluene reflux; the 4,5-cis products proved to be predominantly formed and were isolated. Whereas shortened reaction times were observed by using microwave irradiation or catalytic cuprous chloride, no significant stereoselectivity change was in general noticed. Reacting 2,2-dicyano-3-aryloxiranes with 2-cyclopentenone next afforded 3-aryl-4-oxohexahydro-1H-cyclopenta[c]furan-1,1-dicarbonitriles, and the endo stereoisomers were isolated. That no stereoselectivity change was noticed in the presence of cuprous chloride rather suggests an impac…

Epoxide010402 general chemistryenones01 natural sciencesMedicinal chemistryAnalytical ChemistryCatalysisInorganic Chemistrychemistry.chemical_compound[SDV.SP.MED]Life Sciences [q-bio]/Pharmaceutical sciences/MedicationCascade reaction[3+2] cycloadditionEnamines[CHIM]Chemical SciencesTetrahydrofuransSpectroscopytheoretical calculationschemistry.chemical_classification[CHIM.ORGA]Chemical Sciences/Organic chemistry010405 organic chemistryOrganic ChemistryRegioselectivityCycloaddition0104 chemical sciencescarbonyl ylideschemistryYlide[SDV.MP.VIR]Life Sciences [q-bio]/Microbiology and Parasitology/VirologyStereoselectivityCis–trans isomerismJournal of Molecular Structure
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CCDC 688220: Experimental Crystal Structure Determination

2017

Related Article: Samira Hamza-Reguig, Ghenia Bentabed-Ababsa, Luis R. Domingo, Mar Ríos-Gutiérrez, Stéphanie Philippot, Stéphane Fontanay, Raphaël E. Duval, Sandrine Ruchaud, Stéphane Bach, Thierry Roisnel, Florence Mongin|2018|J.Mol.Struct.|1157|276|doi:10.1016/j.molstruc.2017.12.052

Space GroupCrystallography4-benzoyl-5-(4-methoxyphenyl)-3-phenyldihydrofuran-22(3H)-dicarbonitrileCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 688217: Experimental Crystal Structure Determination

2017

Related Article: Samira Hamza-Reguig, Ghenia Bentabed-Ababsa, Luis R. Domingo, Mar Ríos-Gutiérrez, Stéphanie Philippot, Stéphane Fontanay, Raphaël E. Duval, Sandrine Ruchaud, Stéphane Bach, Thierry Roisnel, Florence Mongin|2018|J.Mol.Struct.|1157|276|doi:10.1016/j.molstruc.2017.12.052

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters4-oxo-3-phenylhexahydro-1H-cyclopenta[c]furan-11-dicarbonitrileExperimental 3D Coordinates
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