Tarasenko K. Synthesis and properties of phosphorous containing compounds based on В-(alkoxy,amino)vinyl polyfluoroalkyl ketones

Polyftoralcylphosphates and phosphonates. Reactivity and reaction direction of В-alcoxysubstituted compounds in the relation to phosphites; synthesis before unknown persons fluorcontainig phosphates and phospyonates; studying of an opportunity of application of the received connections in synthesis nitrogen heterocyclic, containing phosphates or polyfluoralcyl groups. Organic synthesis, РMR-spectroscopy on nucleus 1H, 13C, 31P, 19F, mass-spectrometry, element analysis, column and thin-layer chromatography, HPLC. It was shown that reactivity and reaction direction (Perkow reaction, Arbuzov reaction) depends considerably on starting material structure. ?-Alkoxysubstituted compounds (enones) with bromine atom in ?-position gave after reaction only fluorocontaining phosphates (Perkow rearrangement products), whereas ?-aminosubstituted compounds (enaminones) containing bromine atom in ?-position react with triethylphosphite according to Arbuzov protocol formed fluorocontaining phosphonates. The reactivity of obtained fluorinated phosphonates in heterocyclization reactions was researched on an example of trifluoromethyl containing phosphonate. As a result new five- and six-membered heterocycles bearing trifluoromethyl group and phosphonate function (perspective precursors for HEW olefination) were synthesized. The reactivity of synthesized fluorinated dienyl phosphates in the Diels-Alder reaction was researched on an example of bromosubstituted dienyl phosphate. It was found the compound doesn't react with dienophiles in various temperature in various solvents, but reacts with methyl vinyl ketone in the presence of SnCl4 with high selectivity. Primary data of insecticidal activity of synthesized phosphates were evaluated. It was found that synthesized fluorinated phosphates are perspective insecticides. Sphere of the use is bioorganic chemistry.