0000000000349751
AUTHOR
Thierry Roisnel
showing 10 related works from this author
A combined experimental and theoretical study of the polar [3+2] cycloaddition of electrophilically activated carbonyl ylides with aldehydes and imin…
2009
International audience; Numerous 2,5-diaryl-1,3-dioxolane-4,4-dicarbonitriles and 2,4-diphenyl-1,3-oxazolidine-5,5- dicarbonitriles have been synthesized by [3+2] cycloaddition reactions between carbonyl ylides generated from epoxides, and aldehydes or imines. In contrast to the use of aldehydes (3,4,5- trimethoxybenzaldehyde, piperonal, 1-naphthaldehyde, indole-3-carboxaldehyde, furan-2- carboxaldehyde and thiophene-2-carboxaldehyde), the reactions performed with imines (N- (phenylmethylene)methanamine, N-(1,3-benzodioxol-5-ylmethylene)propylamine, N-(1,3-benzodioxol- 5-ylmethylene)butylamine and N-(1,3-benzodioxol-5-ylmethylene)benzylamine) proceed diastereoselectively. The effect of micr…
New Multidimensional Coordination Polymers with μ 2 ‐ and μ 3 ‐dcno Cyano Carbanion Ligand {dcno – = [(NC) 2 CC(O)O(CH 2 ) 2 OH] – }
2006
New polymeric materials [M(dcno)2(H2O)2] [M = FeII (1), CoII (2)] and [M(dcno)2] [M = CuII (3), MnII (4)] with dcno– =[(NC)2CC(O)O(CH2)2OH]– = 2,2-dicyano-1-(2-hydroxyethoxy)ethenolate anion have been synthesised and characterised by IR spectroscopy, X-ray crystallography and magnetic measurements. In compounds 1 and 2, each organic ligand acts in a bridging mode with its two nitrogen atoms bound to two different metal ions, while in compounds 3 and 4, each organic anion acts as a μ3-bridging ligand through its two nitrogen atoms and the oxygen atom of the OH group. Each metal ion has a pseudo-octahedral trans-MN4O2 environment with four nitrogen atoms from four different organic ligands an…
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.
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…
Polar [3 + 2] cycloaddition of ketones with electrophilically activated carbonyl ylides. Synthesis of spirocyclic dioxolane indolinones
2008
International audience; The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and ketones (ethyl pyruvate, ethyl phenylglyoxylate, isatin, N-methylisatin and 5-chloroisatin) to give substituted dioxolanes and spirocyclic dioxolane indolinones was investigated. The effect of microwave irradiation on the outcome of the reaction was studied. The thermal reaction between 2,2-dicyano-3-phenyloxirane and N-methylisatin was theoretically studied using DFT methods. This reaction is a domino process that comprises two steps. The first is the thermal ring opening of the epoxide to yield a carbonyl ylide intermediate, whereas the second step is a polar [3 + 2] cycloadditio…
A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes.
2011
International audience; Reactions were performed from aryl azides on the one hand, and activated alkenes coming from β-dicarbonyl compounds or malonodinitrile on the other hand, either with recourse to conventional heating or to microwave activation, to afford 1-aryl-1H-1,2,3-triazoles. The mechanism and the regioselectivity of the reactions involving β-dicarbonyl compounds have been theoretically studied using DFT methods at the B3LYP/6-31G* level: they are domino processes comprising a tautomeric equilibrium of the β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower acti…
Functionalization of Porphyrins: Mechanistic Insights, Conformational Studies, and Structural Characterizations
2006
The condensation of 3-chloromethylbenzoyl chloride with three atropisomers of meso-5,10,15,20-tetrakis(2-aminophenyl)porphyrin (TAPP) is reported, followed by the reaction of the anion of diethyl malonate to prepare various strapped porphyrins. According to two different geometries of the straps, the resulting preorganization of the hanging ethoxycarbonyl groups is more or less adapted to the coordination of cations such as lanthanides. The conformational study, as well as the X-ray structures of three strapped porphyrins, demonstrate that among the three atropisomers investigated in this work, only two of them lead to strapped porphyrins in which an ethoxycarbonyl group is directed towards…
A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines
2015
International audience; Ammonium bifluoride was efficiently used (at a 0.5 mol % loading) to catalyze the cyclocondensation between 1,2-arylenediamines and 1,2-dicarbonyl compounds at room temperature in methanol-water, affording quinoxalines and pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by reacting aryl glyoxals with 3-methyl-1,2-phenylenediamine and 2,3-diaminopyridine, respectively. Analysis of the DFT reactivity indices allowed to explain the catalytic role of ammonium bifluoride.
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
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