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10.1002/ejoc.202000518
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Título: | The Elusive 1,4-Diazabutatrienes: Lurking in the Shadows |
Fecha de publicación: | 8-sep-2020 |
Cita bibliográfica: | European Journal of Organic Chemistry, 2020, 2020, 5496 - 5500 |
ISSN: | 1434-193X |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | 1,4-diazabutatriene dimerization isocyanides reaction mechanism |
Resumen: | Isocyanides are isomers of cyanides in which its terminal carbon atom can exist in a divalent state. Their ambivalent electronic nature as nucleophile or electrophile and wide reactivity turn the isocyanide scaffold in a valuable synthon for the synthesis of structurally complex molecules, in particular azacycles. Although they are known to polymerize easily, the dimerization of isocyanides affording head-to-head dimers, namely 1,4-diazabutatrienes R1-N=C=C=N-R1, has been scarcely explored. Nowadays the experimental isolation of this kind of heterocumulenes is still a challenge. In this minireview, covering a period of sixty years, we highlight the role of 1,4-diazabutatienes as putative reaction intermediates in the homo- and heterodimerization of different types of isocyanides. Added to this, we revise a set of reported reactions in which the formation of a transient 1,4-diazabutatriene intermediate has not been proposed but could be considered as a plausible alternative. |
Autor/es principal/es: | Marin-Luna, Marta Alajarín, Mateo |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica Facultades, Departamentos, Servicios y Escuelas::Facultades de la UMU::Facultad de Química |
Versión del editor: | http://doi.wiley.com/10.1002/ejoc.202000518 |
URI: | http://hdl.handle.net/10201/113623 |
DOI: | 10.1002/ejoc.202000518 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 6 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Aparece en las colecciones: | Artículos: Química Orgánica |
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Marin-Luna_2020EurJOC5496.pdf | 1,36 MB | Adobe PDF | Visualizar/Abrir |
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