New synthesis of 2-heteroarylperfluoropropionic acids derivatives by reaction of azine N-oxides with hexafluoropropene

Chemistry : a European Journal
Rafał Loska, Mieczysław Makosza

Abstract

Hexafluoropropene reacts with aromatic azine N-oxides under mild conditions to produce fluorides of 2-heteroarylperfluoropropionic acids. The reaction proceeds as 1,3-dipolar cycloaddition followed by spontaneous scission of the N--O bond in the isoxazolidine ring and elimination of HF. When the reaction is carried out in the presence of alcohols or N-alkyl anilines, the in situ formed acyl fluorides give the corresponding esters and amides. They can be also treated separately with nucleophiles to produce the respective acylation products, whereas their hydrolysis leads to unstable carboxylic acids that undergo spontaneous decarboxylation to 1-aryl-1,2,2,2-tetrafluoroethanes. This new reaction provides a simple and general method of synthesizing 2-heteroarylperfluoropropionic acid derivatives that were previously unknown and unavailable.

Citations

Dec 15, 2015·Journal of the American Chemical Society·Lennart BrewitzMasakatsu Shibasaki
Aug 20, 2015·Organic & Biomolecular Chemistry·Rafał Loska, Patrycja Bukowska
May 4, 2016·Organic & Biomolecular Chemistry·Giacomo E M CrisenzaJohn F Bower
Jan 7, 2017·The Journal of Organic Chemistry·Ya-Ping HanYong-Min Liang
Mar 7, 2018·Angewandte Chemie·Wang ZhouMasahiro Murakami
Dec 21, 2019·The Journal of Physical Chemistry. a·Paulina MechMariusz Makowski
Jan 7, 2020·The Journal of Organic Chemistry·Dongeun KimIn Su Kim

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