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

Authors :: Aksenov AV
Aksenov NA
Kirilov NK
Skomorokhov AA
Aksenov DA
Kurenkov IA
Sorokina EA
Nobi MA
Rubin M
Source :: RSC advances [RSC Adv] 2021 Nov 04; Vol. 11 (57), pp. 35937-35945. Date of Electronic Publication: 2021 Nov 04 (Print Publication: 2021).
Publication Year :: 2021
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.<br />Competing Interests: There are no conflicts to declare.<br /> (This journal is © The Royal Society of Chemistry.)

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