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New Synthesis of 2‐Heteroarylperfluoropropionic Acids Derivatives by Reaction of Azine N ‐Oxides with Hexafluoropropene
Author(s) -
Loska Rafał,
Mąkosza Mieczysław
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701416
Subject(s) - chemistry , azine , nucleophile , cycloaddition , decarboxylation , hydrolysis , organic chemistry , medicinal chemistry , alkyl , acylation , bond cleavage , catalysis
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 NO 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.