Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study

ABSTRACT: [2 + 3] Cycloaddition reactions of nitroacetylene with allenyl-type three-atom components take place according to the polar, but a one-step mechanism. Alternatively to cycloadducts, during the reaction between the aforementioned reagents, zwitterionic structures with “extended” conformatio...

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Detalles Bibliográficos
Autor principal: Jasiński, Radomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2015
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4495019/
https://www.ncbi.nlm.nih.gov/pubmed/26166899
http://dx.doi.org/10.1007/s00706-014-1389-0
Descripción
Sumario:ABSTRACT: [2 + 3] Cycloaddition reactions of nitroacetylene with allenyl-type three-atom components take place according to the polar, but a one-step mechanism. Alternatively to cycloadducts, during the reaction between the aforementioned reagents, zwitterionic structures with “extended” conformation may be formally created. However, this route is supported by neither kinetic nor thermodynamic factors. GRAPHICAL ABSTRACT: [Image: see text]

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