Action du chlorure d'acetyle et de l'anhydride acetique sur le nitronate de lithium derive du phenyl-2 nitroethane : Reactivite electrophile ou dipolaire,en fonction du milieu,de l'oxyde de nitrile intermediairement forme |
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| Institution: | 1. Cardiology Department, Hôpital Croix-Rousse and Hôpital Lyon Sud, Hospices Civils de Lyon, Lyon, France;2. University of Lyon, CREATIS UMR5220, INSERM U1044, INSA-15 Lyon, France;3. Cardiology Service, Rouen–Charles-Nicolle University Hospital Center, National Institute of Health and Medical Research U644, Rouen, France;4. Service de Biostatistique et Bioinformatique, University of Lyon, CNRS UMR 5558, Laboratoire de Biométrie et Biologie Evolutive, Equipe Biostatistique-Santé, F-69100 Villeurbanne, France;5. Department of Cardiology, Gabriel Montpied University Hospital Center, Image Science for Interventional Techniques, Cardiovascular Interventional Therapy and Imaging, National Scientific Research Center UMR 6284, University of Auvergne, Clermont-Ferrand, France;6. Radiology Department, Hôpital Croix-Rousse, Hospices Civils de Lyon, Lyon, France;7. Institut Cardiovasculaire Paris Sud, Ramsay - Générale de Santé, France |
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| Abstract: | The lithium nitronate salt derived from 2-phenyl nitroethane reacts with acetic anhydride and with acetyl chloride to give an intermediate nitrile oxide. Depending on the protonating character of the medium, this latter can react either as a 1,3 dipole to give the furoxan or, in the presence of a dipolarophile, the corresponding adduct ; or as an electrophile leading to the chlorooxime or to derivatives of benzohydroxamic acid. The formation of the nitrile oxide, by loss of acetic acid from a nitronic-acetic mixed anhydride, appears to be the most plausible reaction pathway accounting for the above observations. |
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