Preparation and ESR characterization of polyalkyl-s-indacenyl anion-radicals from polyalkyl-1,5-dilithio-s-indacenes |
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Authors: | C. Adams,C. Morales,J.M. Manriquez,N. Katir,P. Riviè re,M. Riviè re-Baudet,N. Gatica |
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Affiliation: | a Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Correo 22, Santiago de Chile, Chile b Departamento de Química, Universidad Andres Bello, República 275, Santiago de Chile, Chile c Laboratoire d’Hétérochimie Fondamentale et Appliquée, UMR 5069 du CNRS, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse Cedex 94, France d Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Casilla 160-C, Concepción, Chile |
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Abstract: | Polyalkyl-(or chloropolyalkyl)-s-indacenyl anion radicals were obtained from the organodilithium derivatives of the corresponding substituted-1,5-dihydro-s-indacenes by three different methods: (i) UV photolysis, (ii) oxidation by a ferrocenium salt, (iii) single electron transfer reaction from an electron rich olefin. The last reaction (iii) involves transient formation of an unstable polyalkyl-lithio-s-indacenyl imidazolidinium salt. The same salt, obtained by another way by reacting 1,3-dimethylimidazolidinium chloride with the polyalkyl-1,5-dilithio-s-indacene, also leads to the corresponding lithium polyalkyl-s-indacenyl anion radical. All lithium polyalkyl-s-indacenyl anion radicals studied were characterized from their ESR spectra. They present a characteristic symmetrical spin distribution. On the contrary a Rhodium-COD polyalkyl-s-indacene radical presents a non symmetrical spin distribution. |
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Keywords: | Polyalkyl-(or chloropolyalky)l-s-indacenyl anion radicals ESR 1,1&prime ,2,2&prime -Tetramethyl-2,2&prime -bisimidazolidine Polyalkyl-lithio-s-indacenylimidazolidinium salt |
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