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...

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Veröffentlicht in:	RSC advances 2021-11, Vol.11 (57), p.35937-35945
Hauptverfasser:	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
Format:	Artikel
Sprache:	eng
Schlagworte:	Adducts Chemistry Chemistry, Multidisciplinary Physical Sciences Reagents Science & Technology
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Zusammenfassung:	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. 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?
ISSN:	2046-2069 2046-2069
DOI:	10.1039/d1ra06503c