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; Michael Rubin

doi:10.1039/D1RA06503C

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

Alexander V. Aksenov,

*^a Nicolai A. Aksenov,

^a Nikita K. Kirilov,^a Anton A. Skomorokhov,^a Dmitrii A. Aksenov,

^a Igor A. Kurenkov,

^a Elena A. Sorokina,

^b Mezvah A. Nobi^c and Michael Rubin

*^ac

Author affiliations

* Corresponding authors

^a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia
E-mail: aaksenov@ncfu.ru

^b Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya St., Moscow, Russian Federation

^c Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, USA
E-mail: mrubin@ku.edu

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.

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DOI: https://doi.org/10.1039/D1RA06503C
Article type: Paper
Submitted: 28 Aug 2021
Accepted: 27 Oct 2021
First published: 04 Nov 2021
This article is Open Access

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RSC Adv., 2021,11, 35937-35945

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

A. V. Aksenov, N. A. Aksenov, N. K. Kirilov, A. A. Skomorokhov, D. A. Aksenov, I. A. Kurenkov, E. A. Sorokina, M. A. Nobi and M. Rubin, RSC Adv., 2021, 11, 35937 DOI: 10.1039/D1RA06503C

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

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