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2. Dynamics of the Lithium Amide/Alkyllithium Interactions: Mixed Dimers and Beyond

Author

Harrison-Marchand, Anne, Duguet, Nicolas, Barozzino-Consiglio, Gabriella, Oulyadi, Hassan, Maddaluno, Jacques, Beller, Matthias, Series editor, Brown, John M., Series editor, Dixneuf, Pierre H., Series editor, Dupont, Jairton, Series editor, Fürstner, Alois, Series editor, Gooßen, Lukas J., Series editor, Ikariya, Takao, Series editor, Nolan, Steve, Series editor, Oro, Luis A., Series editor, Zhou, Qi-Lin, Series editor, Okuda, Jun, Series editor, and Xi, Zhenfeng, editor

Published
2014
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17. Enzymatic Synthesis of Aliphatic Acyloins through Thermostable Transketolase Catalyzed-Reaction

Author

Casajus, Hubert, Lagarde, Aurélie, Leremboure, Martin, Dios Miguel, Thomas De, Nauton, Lionel, Thery, Vincent, Fessner, Wolf-Dieter, Duguet, Nicolas, Charmantray, Franck, Hecquet, Laurence, Institut de Chimie de Clermont-Ferrand (ICCF), SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Technische Universität Darmstadt (TU Darmstadt), Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Technische Universität Darmstadt - Technical University of Darmstadt (TU Darmstadt)

Subjects
[CHIM]Chemical Sciences, [CHIM.CATA]Chemical Sciences/Catalysis
Abstract

International audience; Thermostable TKgst was successfully engineered for the synthesis of aliphatic acyloins with various carbon backbone lengths (C5-C10). Based on structure guided studies, efficient TKgst variants with enhanced activities toward aliphatic aldehydes as acceptors together with aliphatic pyruvate homologues as donors were identified. The TKgst single variant L382F was able to catalyze efficiently the transfer of the ketol group from HPA on all targeted aliphatic aldehydes (C3-C8) to give the corresponding 1,3-dihydroxy ketones with good yields and excellent enantioselectivity. The combination of H102L/H474S previously designed for the improvement toward aliphatic pyruvate homologues, with F435I gave a new variant H102L/H474S/F435I able to transfer the acyl goup of 2-oxobutyrate and 2-oxovalerate to aliphatic aldehydes, giving mono hydroxylated ketones never obtained before with this enzyme.

Published
2020
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18. A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO 2 into Cyclic Carbonates

Author

Grollier, Kevin, Vu, Nam Duc, D'Agosto, Franck, Duc Vu, Nam, Onida, Killian, Akhdar, Ayman, Norsic, Sébastien, Agosto, Franck, Boisson, Christophe, Duguet, Nicolas, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265 (C2P2), and Université de Lyon-Université de Lyon-École supérieure de Chimie Physique Electronique de Lyon (CPE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
epoxides, 010405 organic chemistry, Polyethylene, Organocatalysis, carbon dioxide, [CHIM]Chemical Sciences, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, cyclic carbonates, 010402 general chemistry, 7. Clean energy, 01 natural sciences, 0104 chemical sciences
Abstract

International audience; An imidazolium catalyst supported on thermomorphic polyethylene (PE) was prepared from 1methylimidazole and polyethylene iodide (PE-I). The catalyst was characterized by 1 H and 13 C NMR, SEC and MALDI-ToF mass spectrometry. Its catalytic activity was evaluated in the ring-opening of epoxides with carbon dioxide to give cyclic carbonates under solvent-free conditions. The catalyst proved to be active at low catalyst loading (down to 0.1 mol%) and allows the reaction to occur at low CO2 pressure (1-5 bar) and moderate temperature (100°C). A range of terminal and internal epoxides was converted to the corresponding cyclic carbonates with high yields and selectivities. The recyclability of the catalyst was studied and no significant loss of activity was observed after 5 runs.

Published
2020
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20. Origin of the detrimental effect of lithium halides on an enantioselective nucleophilic alkylation of aldehydes

Author

Pate, Franck, Duguet, Nicolas, Oulyadi, Hassan, Harrison-Marchand, Anne, Fressigne, Catherine, Valnot, Jean-Yves, Lasne, Marie-Claire, and Maddaluno, Jacques

Subjects
Lithium compounds -- Chemical properties, Enantiomers -- Chemical properties, Chirality -- Analysis, Biological sciences, Chemistry
Abstract

The effect of lithium halides on the enantioselectivity of the addition of methyllithium on o-tolualdehyde is examined. The results have shown that a sequestration of the source of chirality by the lithium halides is at the origin of the detrimental effect of the additives on the ee of the model reaction.

Published
2007

28. Synthesis of Fatty 1,2,4-Trioxanes by Peracetalization of β-Hydroxy Hydroperoxides.

Author

De Dios Miguel, Thomas, Louvel, Dan, Onida, Killian, Lavoignat, Adeline, Picot, Stephane, and Duguet, Nicolas

Subjects
HETEROGENEOUS catalysts, ACID catalysts, METHYL ether, PLASMODIUM falciparum, HYDROPEROXIDES, BENZALDEHYDE, SULFONIC acids, AROMATIC aldehydes
Abstract

The peracetalization of a β-hydroxy hydroperoxide derived from methyl oleate was studied using benzaldehyde as a model substrate to give the corresponding fatty 1,2,4-trioxane. The desired product was obtained as a mixture of regioisomers but only one diastereoisomer of each was formed. The nature of the acid catalyst was studied and both p -toluene sulfonic acid (PTSA) and Amberlyst A35 (A35) were found to be efficient homogeneous and heterogeneous catalysts, respectively. The nature of the solvent was also investigated and ethereal solvents such as 2-methyltetrahydrofuran (2-MeTHF), methyl tert -butyl ether (MTBE) and cyclopentyl methyl ether (CPME) gave the best NMR yield (85%) for the preparation of the fatty trioxane. The optimized conditions were applied to a range of aromatic and aliphatic aldehydes, and the corresponding 1,2,4-trioxanes were isolated with 30–91% yields (21 examples). The antimalarial activity of three trioxanes was studied against Plasmodium falciparum, however, no significant activity was detected (IC50 >1600 nM). [ABSTRACT FROM AUTHOR]

Published
2022
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29. Solvent-Free N-Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica-Alumina

Author

Charvieux, Aubin, Le Moigne, Louis, Borrego, Lorenzo, Duguet, Nicolas, Métay, Estelle, Catalyse Synthèse et Environnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), and Université de Lyon

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; The N-alkylation of phenylacetamide with benzyl alcohol has been studied using Ni/SiO2-Al2O3. In the optimized conditions, the desired product was isolated in an excellent 98% yield. The reaction could advantageously be performed in neat conditions, with a slight excess of amide and a catalytic amount of base. These conditions were tested on a large range of amides and alcohols, affording 24 compounds in 13 to 99% isolated yields.

Published
2019
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31. Valorization of Methyl Azelaaldehydate - A Vegetable Oil Based Platform Molecule for the Synthesis of Monomers through Stetter Reaction

Author

Charvieux, Aubin, Duc Vu, Nam, Duguet, Nicolas, Lemaire, Marc, Catalyse Synthèse et Environnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019
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36. Thermomorphic Polyethylene‐Supported Organocatalysts for the Valorization of Vegetable Oils and CO2.

Author

Akhdar, Ayman, Onida, Killian, Vu, Nam Duc, Grollier, Kevin, Norsic, Sébastien, Boisson, Christophe, D'Agosto, Franck, and Duguet, Nicolas

Subjects
VEGETABLE oils, RAPESEED oil, CATALYSTS recycling, CATALYTIC activity, CARBONATES, FATTY acids, CARBONATE minerals
Abstract

A range of thermomorphic polyethylene‐supported organocatalysts is prepared from N‐alkyl imidazoles and polyethylene iodide (PEI) with good yields (85–92%) and high funtionality (98–99%). The catalytic activity of these species is studied for the ring opening of epoxidized methyl oleate with CO2 to give the corresponding cyclic carbonate. The reaction is carried out at 100 °C to fully exploit the thermomorphic behavior of the organocatalysts. The optimized conditions (neat, 100 °C, and 20 bar of CO2) are applied to a range of epoxidized fatty acids, including an epoxidized rapeseed oil, to give the corresponding carbonates with good yields (75–96%). The catalyst recycling is also studied, and no significant loss of activity is observed after ten runs. The fatty carbonates are important intermediates for the preparation of non‐isocyanate polyurethanes (NIPUs). [ABSTRACT FROM AUTHOR]

Published
2021
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37. Le développement durable à découvert

Author

Abbadie, Luc, Alger, Ingela, André, Michel, Annesi-Maesano, Isabella, Arnaud, Nicolas, Arnould, Paul, Atteia, Olivier, Auffray, Jean-Christophe, Barles, Sabine, Barnaud, Geneviève, Baron, Nacima, Barraqué, Bernard, Battin-Leclerc, Frédérique, Baudry, Jacques, Benoît, Marc, Berthoud, Françoise, Bertin, Xavier, Bès, Clémence, Blain, Stéphane, Blanc, Isabelle, Blanc, Nathalie, Boëtsch, Gilles, Boeuf, Gilles, Bondeau, Alberte, Bopp, Laurent, Bornette, Gudrun, Boutigny, Dominique, Bretagnolle, Vincent, Brunet, Yves, Burel, Françoise, Capy, Pierre, Cassir, Michel, Cathelineau, Michel, Chalon, Jean-Pierre, Chanéac, Corinne, Chemineau, Philippe, Chevaldonné, Pierre, Clergeau, Philippe, Colonna, Paul, Comby, Joseph, Coulon, Jean-Baptiste, Coutard, Olivier, Couvet, Denis, Cramer, Wolfgang, Crifo, Patricia, Cury, Philippe, Dandin, Philippe, David, Romain, Da Silva, Éric, Delecluse, Pascale, Delmotte, Valérie Masson, Desjardins, Xavier, Dessaux, Yves, de Marsily, Ghislain, Diaconu, Cristinel, Djellouli, Yamna, Dobré, Michelle, Douville, Hervé, Dron, Dominique, Dufumier, Marc, Duguet, Nicolas, Dutoit, Thierry, Duvat, Virginie, Ekeland, Ivar, Emelianoff, Cyria, Esnouf, Catherine, Euzen, Agathe, Eymard, Laurence, Féral, Jean-Pierre, Foyer, Jean, Frossard, Victor, Fuchs, Alain, Gaill, Françoise, Gaillard, Émilie, Galgani, François, Garnier, Emmanuel, Garric, Jeanne, Garrigues, Philippe, Geoffron, Patrice, George, Christian, Ghorra-Gobin, Cynthia, Gilbert, Claude, Goffé, Bruno, Gondran, Natacha, Grison, Claude, Guermont, Catherine, Guihard-Costa, Anne-Marie, Hainzelin, Étienne, Harpet, Cyrille, Hervé-Fournereau, Nathalie, Hourcade, Jean-Charles, Ingold, Alice, Isnard, Laure, Jeandel, Catherine, Jessus, Catherine, Joussaume, Sylvie, Jullian, Sophie, Kaisermann, Aurore, Labussière, Olivier, Lageat, Yannick, Larrère, Catherine, Larrue, Corinne, Lata, Jean-Christophe, Laugier, Sandra, Lavorel, Sandra, Leadley, Paul, Leblois, Antoine, Lemaire, Marc, Lepart, Jacques, Letonturier, Éric, Levi, Yves, Lévy, Jean-Pierre, Lévy, Marina, Le Bohec, Céline, Le Bras, Hervé, Le Maho, Yvon, Le Roux, Thomas, Le Treut, Hervé, Longaretti, Pierre-Yves, Loreau, Michel, Lucas, Hélène, Lucotte, Marc, Magny, Michel, Marco, Audrey, Massot, Marie-Hélène, Mathevet, Raphaël, Mayaud, Jean-Luc, Mellouki, Abdelwahid, Merlot, Bérengère, Métay, Estelle, Meyer, Morgan, Millet, Laurent, Mosseri, Rémy, Muller, Bertrand, Nadaï, Alain, Negrutiu, Ioan, Ngô, Christian, Ogé, Frédéric, Olivieri, Isabelle, Pacteau, Chantal, Paillard, Sandrine, Papon, Pierre, Pavé, Alain, Pérez, Thierry, Perrodin, Yves, Pironon, Jacques, Planes, Serge, Pomel, Simon, Pont, Didier, Quirion, Philippe, Reghezza-Zitt, Magali, Rémond, Yves, Renaud, François, Rochette, Julien, Ronce, Ophélie, Roué, Marie, Royer, Michel, Russel, Marie, Salanié, François, Salles, Denis, Salles, Jean-Michel, Sanchez, Clément, Sardin, Michel, Schmitt, Bertrand, Sonnemann, Guido, Souami, Taoufik, Soussou, Tatongueba, Sultan, Benjamin, Tatoni, Thierry, Thibaud, Jean-Paul, Thiébault, Stéphanie, Thomas, Frédéric, Tixier-Boichard, Michèle, Toulhoat, Hervé, Tourre, Yves, Toussaint, Jean-Yves, Treyer, Sébastien, Troussellier, Marc, Tubiana, Laurence, Vareilles, Sophie, Velut, Sébastien, Verneaux, Valérie, Viard, Jean, Vidal, Olivier, Villalba, Bruno, Villenave, Éric, Vindimian, Éric, Vlassopoulos, Chloé Anne, Voltz, Marc, Weber, Christiane, Weber, Jacques, Weisbuch, Claude, Wöppelmann, Guy, Yiou, Pascal, Laboratoire Techniques, Territoires et Sociétés (LATTS), and Université Paris-Est Marne-la-Vallée (UPEM)-École des Ponts ParisTech (ENPC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
2. Zero hunger, 0106 biological sciences, conservation des ressources naturelles, restauration de l'environnement, [SHS.SOCIO]Humanities and Social Sciences/Sociology, RNK, écologie humaine, Non précisé, 010501 environmental sciences, 01 natural sciences, environnement, NAT011000, politique environnementale, 13. Climate action, développement durable, Environmental studies, Geography & Development, santé, 010606 plant biology & botany, 0105 earth and related environmental sciences
Abstract

Vingt ans après la première conférence de Rio, qu'est devenue la proposition de conduire nos sociétés vers un développement durable ? Adopté par les uns, utilisé comme faire-valoir par les autres, ce concept de développement durable est souvent vidé de son sens. Or, l'impact exponentiel des activités humaines sur les ressources naturelles, la santé des populations et le milieu exige d'expliquer ce qu'il est précisément. Qu'est-ce que le développement durable aujourd'hui ? Qu'en est-il de la disponibilité des ressources et de l'usage que nous en faisons ? Dans le domaine de l'eau, du climat, des sols, de la biodiversité ? En milieu rural, sur le littoral ou encore en milieu urbain, là où la majorité de la population va vivre d'ici 2050, comment consommons-nous au fil du temps, à travers les territoires? Quelles incidences les activités humaines ont-elles sur les ressources, sur la santé des populations et sur le milieu lui-même ? Les relations entre l'humanité et l'environnement doivent-elles évoluer ? Autant de questions posées à des scientifiques qui éclaircissent la complexité des interactions entre les systèmes et proposent des solutions pour un avenir sur le long terme. De nos écosystèmes à nos modes de consommation, des risques naturels aux nouvelles technologies ou aux pollutions, des usines du futur au traitement des déchets, Le développement durable à découvert informe, explique, partage tout ce que la science actuelle est capable d'apporter au défi majeur du XXIe siècle : comment mieux comprendre la complexité des enjeux qui nous concernent tous et assurer le développement de l'humanité sans détruire son biotope. Économistes, physiciens, sociologues, agronomes, écologues... plus de 150 chercheurs se sont mobilisés pour associer leur expertise à leur regard critique et décrire, comprendre, modéliser, imaginer, illustrations et schémas à l'appui, les outils destinés à construire les sociétés équitables de demain.(résumé 4e de couv)

Published
2017

38. 12. La chimie verte

Author

Métay, Estelle, Duguet, Nicolas, Da Silva, Éric, and Lemaire, Marc

Abstract

Ce qu’il est convenu d’appeler « chimie verte » ou « durable » ou « écologique » regroupe des concepts et des technologies ayant recours à des matières premières renouvelables. Cet ensemble a conduit à des pratiques industrielles et scientifiques très différentes de celles qui ont fait les immenses succès de la chimie du XXe siècle (amélioration et préservation de la vie) et parfois ses terribles conséquences (accidents, pollutions, contaminations…). La chimie, à la fois science et industrie,...

Published
2017

39. Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β‐Hydroxy Hydroperoxides.

Author

De Dios Miguel, Thomas, Duc Vu, Nam, Lemaire, Marc, and Duguet, Nicolas

Subjects
EPOXY compounds, MOLYBDENUM catalysts, ALDEHYDES, TUNGSTEN catalysts, HYDROPEROXIDES, DIFFERENTIAL scanning calorimetry, TUNGSTEN alloys
Abstract

The ring‐opening of epoxidized methyl oleate by aqueous H2O2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty β‐hydroxy hydroperoxides. It was found that tungstic acid and phosphotungstic acid gave the highest selectivities (92–93 %) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2‐diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty β‐hydroxy hydroperoxides with 30–80 % isolated yields (8 examples). These species were fully characterized by 1H and 13C NMR spectroscopy and HPLC‐HRMS, and their stability was studied by differential scanning calorimetry. The thermal cleavage of the β‐hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68 % GC yield, and nonanal and methyl 9‐oxononanoate were isolated with 57 and 55 % yield, respectively. Advantageously, the overall process does not require large excess of H2O2 and only generates water as a byproduct. [ABSTRACT FROM AUTHOR]

Published
2021
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40. A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO2 into Cyclic Carbonates.

Author

Grollier, Kevin, Vu, Nam Duc, Onida, Killian, Akhdar, Ayman, Norsic, Sébastien, D'Agosto, Franck, Boisson, Christophe, and Duguet, Nicolas

Subjects
CATALYST supports, CATALYTIC activity, CARBON dioxide, EPOXY compounds, SALTS, CARBONATES
Abstract

An imidazolium catalyst supported on thermomorphic polyethylene (PE) was prepared from 1‐methylimidazole and polyethylene iodide (PE−I). The catalyst was characterized by 1H and 13C NMR, SEC and MALDI‐ToF mass spectrometry. Its catalytic activity was evaluated in the ring‐opening of epoxides with carbon dioxide to give cyclic carbonates under solvent‐free conditions. The catalyst proved to be active at low catalyst loading (down to 0.1 mol%) and allows the reaction to occur at low CO2 pressure (1–5 bar) and moderate temperature (100 °C). A range of terminal and internal epoxides was converted to the corresponding cyclic carbonates with high yields and selectivities. The recyclability of the catalyst was studied and no significant loss of activity was observed after 5 runs. [ABSTRACT FROM AUTHOR]

Published
2020
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44. Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi

Author

Duguet, Nicolas, Petit, Sylvain M., Marchand, Philippe, Harrison-Marchand, Anne, and Maddaluno, Jacques

Subjects
Lithium compounds -- Structure, Lithium compounds -- Chemical properties, Chirality -- Analysis, Tetrahydrofuran -- Structure, Tetrahydrofuran -- Chemical properties, Thiophene -- Structure, Thiophene -- Chemical properties, Biological sciences, Chemistry
Abstract

Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 3-aminotetrahydrothiophens (3ATTs) and 3-aminotetrahydrofurans (3ATFs) are prepared. A general concept is described for rationalizing the process of induction in the presence of organolithium species.

Published
2008

45. Probing the efficiency of N-heterocyclic carbene promoted O- to C-carboxyl transfer of oxazolyl carbonates

Author

Thomson, Jennifer E., Campbell, Craig D., Concellon, Carmen, Duguet, Nicolas, Rix, Kathryn, Slawin, Alexandra M.Z., and Smith, Andrew D.

Subjects
Carbenes -- Structure, Carbenes -- Chemical properties, Carbenes -- Optical properties, Ring formation (Chemistry) -- Analysis, Nuclear magnetic resonance spectroscopy -- Analysis, Biological sciences, Chemistry
Abstract

Screening of a range of azolium salts, bases and solvents for reactivity has shown that triazolinylidenes, generated in situ with KHMDS in THF, has promoted the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency. An improved experimental method is described that has allowed a simplified one-pot reaction protocol to be used with high catalytic efficiency.

Published
2008

48. Polyurethane Thermosets Using Lipidic Poly(α‐Hydroxyketone).

Author

Briou, Benoit, Vu, Nam Duc, Caillol, Sylvain, Robin, Jean‐Jacques, Duguet, Nicolas, Lemaire, Marc, Etienne, Pascal, Bonnet, Laurent, and Lapinte, Vincent

Subjects
CASTOR oil, URETHANE, POLYURETHANE elastomers, HYDROGEN bonding, POLYURETHANES, THERMAL stability, POLYOLS
Abstract

Lipidic polyols based on α‐hydroxyketone reactive groups were investigated for polyurethane thermosets. The reactivity of this peculiar secondary alcohol group in triacylglycerol structure was compared, without use of catalyst, to that of poly(1,2‐diol) triacylglycerol and castor oil to demonstrate the influence of ketone in the α position of the alcohol group in the presence of HDI for the urethanization rate. The kinetic effect of the ketone group was also studied on various lipidic architectures: mono(α‐hydroxyketone) ester, di(α‐hydroxyketone) diester and tri(α‐hydroxyketone) triacylglycerol. The presence of hydrogen bonds in the network coming from urethane, residual alcohol, and ketone in hard segments of PU was discussed and correlated with the thermal stability and the soft mechanical properties of the resulting polyurethane thermosets. [ABSTRACT FROM AUTHOR]

Published
2020
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49. α‐Methylation of Ketones with Methanol Catalyzed by Ni/SiO2‐Al2O3.

Author

Charvieux, Aubin, Duguet, Nicolas, and Métay, Estelle

Subjects
*KETONES, *METHANOL
Abstract

α‐Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2‐Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three‐component cross‐benzylation‐methylation of acetophenone. [ABSTRACT FROM AUTHOR]

Published
2019
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50. α‐Methylation of Ketones with Methanol Catalyzed by Ni/SiO2‐Al2O3.

Author

Charvieux, Aubin, Duguet, Nicolas, and Métay, Estelle

Subjects
KETONES, METHANOL
Abstract

α‐Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2‐Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three‐component cross‐benzylation‐methylation of acetophenone. [ABSTRACT FROM AUTHOR]

Published
2019
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