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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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
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author 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
author_facet 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
author_sort Aksenov, Alexander V.
collection PubMed
description 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.
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spelling pubmed-90432682022-04-28 Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides? 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 RSC Adv Chemistry 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 Royal Society of Chemistry 2021-11-04 /pmc/articles/PMC9043268/ /pubmed/35492804 http://dx.doi.org/10.1039/d1ra06503c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
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
Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title_full Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title_fullStr Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title_full_unstemmed Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title_short Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
title_sort does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9043268/
https://www.ncbi.nlm.nih.gov/pubmed/35492804
http://dx.doi.org/10.1039/d1ra06503c
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