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Issue 8, 2014
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Tri- and tetrafluoropropionamides derived from chiral secondary amines – synthesis and the conformational studies

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Abstract

A convenient procedure for the preparation of tri- and tetrafluoropropionamides derived from R-(+)/S-(−)-N-methyl-1-phenylethylamine and cyclic pyrrolidine derivatives has been described. The X-ray analysis and the theoretical calculations have been used to study conformational analysis of obtained compounds. In contrast to single α-fluorine substituted amides, which preferred anti conformation around the F–C–C[double bond, length as m-dash]O bond, for tetrafluorinated amides the additional trifluoromethyl group forces the conformation of the F–C–C[double bond, length as m-dash]O bond as nearly syn.

Graphical abstract: Tri- and tetrafluoropropionamides derived from chiral secondary amines – synthesis and the conformational studies

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Supplementary files

Article information


Submitted
03 Mar 2014
Accepted
02 Jun 2014
First published
04 Jun 2014

This article is Open Access

New J. Chem., 2014,38, 3819-3830
Article type
Paper
Author version available

Tri- and tetrafluoropropionamides derived from chiral secondary amines – synthesis and the conformational studies

M. Bilska-Markowska, M. Rapp, T. Siodła, A. Katrusiak, M. Hoffmann and H. Koroniak, New J. Chem., 2014, 38, 3819
DOI: 10.1039/C4NJ00317A

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