Issue 8, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2014
Accepted
02 Jun 2014
First published
04 Jun 2014
This article is Open Access
Creative Commons BY license

New J. Chem., 2014,38, 3819-3830

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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