Synytsya O. C-Phosphorylated alkylidene amines with electron acceptor substituents at the nitrogen atom

Object - C-phosphorylated imines, containing acyl, phosphoryl, or sulfonyl goups at the imine nitrogen atom and the study of their chemical properties. Purpose - development of synthesis methods for poorly studied C-phosphorylated imines. Methods - NMR and infrared spectroscopy, thin-layer chromatography, X-ray crystallography, elemental analysis.Two methodological approaches for C-phosphorylated imines have been developed: introduction of phosphonyl group to the compounds already containing C=N bond or formation of azomethyne function starting from ?-phosphorylated alkenylamides and related systems. Several new preparative approaches to imidoyl phosphonates have been developed: phosphorylation of imidoyl chlorides, silylation of phosphorylated alkyl-, alkenyl- or amino-gem-bisphosphonates followed by elimination of hydrogen chloride, trimethylchlorosilane or silyl phosphites . Regularities of the substituents effects in imidoyl phosphonates on of their reaction with dienes and dipolarophiles have been established. A series of untypical rearrangements, involving migrations of chlorine and phosphorus atoms, have been identified. A new strategy of targeted synthesis of synthetically and biologically important derivatives of amino phosphonic acids, based on functionalization of imidoyl phosphonates with various N-, O-, S- and P-centered nucleophiles, has been developed.