ULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL y-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES

13C NMR 31P NMR 1H NMR y-iminophosphonates phosphine oxides E/Z isomerism.

ФАЗОВЫЙ СОСТАВ ТОНКИХ ПЛЕНОК КАРБОНИТРИДА КРЕМНИЯ, ПОЛУЧЕННЫХ ПЛАЗМОХИМИЧЕСКИМ РАЗЛОЖЕНИЕМ КРЕМНИЙОРГАНИЧЕСКИХ СОЕДИНЕНИЙ, КРИСТАЛЛИЧЕСКАЯ СТРУКТУРА КООРДИНАЦИОННОГО ПОЛИМЕРА [Cu2(S-mal)2(bpy)2(H2O)] • 2,5H2O, ...

2015. 56, 1 UDC 548.737:541.67 MULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL t-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES A. Wahbi, H. Slimani, S. Touil Laboratory of Heteroatom Organic Chemistry, Department of Chemistry, Faculty of Sciences of Bizerta, University of Carthage, Jarzouna, Tunisia E-mail: soufiane.touil@fsb.rnu.tn Received August, 21, 2013 We report for the first time the synthesis of t-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with t-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 h 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. <...> In view of the above, and in the continuation of our studies on the preparation and potential synthetic applications of imines [25—27 ], we report here for the first time the synthesis of t-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with t-phosphonylketones. <...> The full characterization of these compounds through their 1H, 31P, and 13C NMR spectra indicated that they were obtained as a mixture of Z and E isomers. <...> It was found that the reaction of these compounds with primary amines performed in refluxing toluene for 48 h, in the presence of a catalytic amount of p-toluenesulfonic acid, led to the formation of t-iminophosphonates and phosphine oxides 2 (Scheme 1). <...> The 1H NMR parameters were as follows: spectral width 6188.1 Hz; acquisition time 2.65 s; digital resolution 0.19 Hz; number of scans 16. <...> All NMR spectra were recorded using a Bruker AC-300 spectrometer operating at and 13C NMR and relative to 85 % H3PO4 (external reference) for 31P NMR. <...> Z and E isomers in compounds 2 The Z and E configurations were attributed on the basis of the 13C chemical shifts of C2 carbon atoms in the h position with respect to the C=N double bond (Tables 2 and 3). <...> Indeed, according to some literature data [ 25, 30—34 <...>

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