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

New Journal of Chemistry Pub Date: 2014-06-04 DOI: 10.1039/C4NJ00317A

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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