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Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?†
Alexander V. Aksenov,Nicolai A. Aksenov,Nikita K. Kirilov,Anton A. Skomorokhov,Dmitrii A. Aksenov,Igor A. Kurenkov,Elena A. Sorokina,Mezvah A. Nobi
RSC Advances Pub Date : 11/04/2021 00:00:00 , DOI:10.1039/D1RA06503C
Abstract

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.

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