MULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL γ-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES
A. Wahbi, H. Slimani, S. Touil
University of Carthage, Jarzouna, Tunisia
Keywords: C NMR
,
P NMR
,
H NMR
, g-iminophosphonates, phosphine oxides, E/Z isomerism,
C NMR
,
P NMR
,
H NMR
, g-iminophosphonates, phosphine oxides, E/Z isomerism
Abstract
We report for the first time the synthesis of γ-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with γ-phosphonylketones. The full characterization of these compounds through their
1H,
31P, and
13C NMR spectra indicates that they are obtained as a mixture of
Z and
E isomers. An unambiguous method for the assignment of these configurations, based on the
13C chemical shifts of C2 carbon atoms in the a position with respect to the C=N double bond is used. The
31P chemical shifts are also of diagnostic importance in assigning the
Z and
E configurations. Indeed, the phosphorus atom is found to resonate at a slightly higher field in
Z isomers.
DOI: 10.1134/S0022476615010060
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