Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?-Reference-Cited by-同舟云学术

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

Published:2021 Issue:57 Volume:11 Page:35937-35945
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Aksenov Alexander V.¹^ORCID,Aksenov Nicolai A.¹^ORCID,Kirilov Nikita K.¹,Skomorokhov Anton A.¹,Aksenov Dmitrii A.¹^ORCID,Kurenkov Igor A.¹^ORCID,Sorokina Elena A.²^ORCID,Nobi Mezvah A.³,Rubin Michael¹³^ORCID

Affiliation:

1. Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

2. Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya St., Moscow, 117198, Russian Federation

3. Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, USA

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?

Funder

Ministry of Education and Science of the Russian Federation

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/RA/D1RA06503C

Reference33 articles.

1. Polystyryl-BEMP as an Efficient Recyclable Catalyst for the Nucleophilic Addition of Nitroalkanes to α,β-Unsaturated Carbonyl Compounds under Solvent-Free Conditions

2. From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes

3. Mechanism and Origins of Stereoselectivity in the Cinchona Thiourea- and Squaramide-Catalyzed Asymmetric Michael Addition of Nitroalkanes to Enones