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 happen, as generated nitrile oxides were successfully intercepted as adducts of [3 + 2] cycloadditions. This journal is © The Royal Society of Chemistry.

Authors
Aksenov A.V. 1 , Aksenov N.A. 1 , Kirilov N.K.1 , Skomorokhov A.A.1 , Aksenov D.A. 1 , Kurenkov I.A.1 , Sorokina E.A. 2 , Nobi M.A.3 , Rubin M. 1, 3
Journal
RSC Advances
Number of issue
57
Language
English
Pages
35937-35945
Status
Published
Link
External link
DOI
10.1039/D1RA06503C
Volume
11
Year
2021
Organizations
  • 1 Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol, 355017, Russian Federation
  • 2 Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 3 Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, United States
Keywords
Chemical activation; Cyanides; Paraffins; Electrophilic activation; Mechanistics; Nitrile oxides; Nitroalkanes; Nucleophilic reagent; Polyphosphoric acids; [3+2]-cycloaddition; Nitrogen oxides
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