0000000000524471
AUTHOR
Samira Hamza-reguig
Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes
[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.
A combined experimental and theoretical study of the thermal [3+2] cycloaddition of carbonyl ylides with activated alkenes
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…
CCDC 688220: Experimental Crystal Structure Determination
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
CCDC 688217: Experimental Crystal Structure Determination
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