Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?

The mechanistic rationale involving activation of nitroalkanes towards interaction with nucleophilic reagents in the presence of polyphosphoric acid (PPA) was re-evaluated. Could nitrile oxide moieties be formed during this process? This experiment demonstrates that at least in some cases this could...

Descripción completa

Detalles Bibliográficos
Autores principales: Aksenov, Alexander V., Aksenov, Nicolai A., Kirilov, Nikita K., Skomorokhov, Anton A., Aksenov, Dmitrii A., Kurenkov, Igor A., Sorokina, Elena A., Nobi, Mezvah A., Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9043268/
https://www.ncbi.nlm.nih.gov/pubmed/35492804
http://dx.doi.org/10.1039/d1ra06503c
Descripción
Sumario:The mechanistic rationale involving activation of nitroalkanes towards interaction with nucleophilic reagents in the presence of polyphosphoric acid (PPA) was re-evaluated. Could nitrile oxide moieties be formed during this process? This experiment demonstrates that at least in some cases this could happen, as generated nitrile oxides were successfully intercepted as adducts of [3 + 2] cycloadditions.

Ejemplares similares