Synthesis and Reaction Peculiarities of Phosphorylated Trifluoroethane Imines

Abstract

Convenient methods for C,N - mono- and biphosphorylated trifluoroethane imines have been developed. These are reactive synthons allowing important derivatives of aminophosphonic acids, fluorine- and phosphorus-containing heterocycles, vinylamides, etc. A rare example of a Perkov-type reaction involving trifluoromethyl group has been discovered.     

Sigmatropic Rearrangements in Phosphorylated 2-Azaallylic Systems

Abstract

Allylic and heteroallylic compounds are classical objects of organic chemistry and can serve as models in the investigation of various theoretical problems. The anions and 1,3-dipoles generated from azaallylic derivatives are widely used in the synthesis of cyclic and acyclic nitrogen-containing compounds.     

Amidoalkylation of Tervalent Phosphorus Chlorides with N-α-Hydroxypolyhalogenoalkyl Amides

Abstract

A new preparative method for synthetically and biologically important N-acyl-, N-phosphoryl-, and N-sulfonylaminopolyhalogenoalkylphosphonyl derivatives 2 is presented.     

First Example of Stereoselective Aza-Perkow Reaction

Russian Journal of General Chemistry -     

Synthesis of α-(acylamino)polyhaloalkylphosphoryl compounds by the reaction of trivalent phosphorus chlorides withN-(α-hydroxypolyhaloalkyl)amides

N-(α-Hydroxypolyhaloalkyl)amides react with trivalent phosphorus chlorides to give α-(acylamino)polyhaloalkylphosphoryl compoundsvia phosphorotropic rearrangement of intermediate phosphites or phosphinites. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1810–1814, September, 1998.     

(N-benzoyl)trichloroacetimidoylphosphonate

A method for the synthesis ofO,O-diethyl (N-benzoyl)trichloroacetimidoylphosphonate (1) by successive reaction ofN-(1-diethoxyphosphoryl-2,2-dichlorovinyl)benzamide with Me₃SiCl and Cl₂ was proposed. The reaction of phosphonate1 with R₃P follows the [4+1] cycloaddition mechanism to give phosphoranes, whose stability and further transformations are controlled by the nature of R. Dedicated to the memory of Academician M. I. Kabachnik on his 90th birthday. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2101–2104, October, 1998.     

Synthesis of phosphorylated 1,3,5‐oxadiazines via N‐acyltrifluoroacetimidoylphosphonates

N‐Benzoyl‐ and N‐methoxycarbonyltrifluoroacetimidoylphosphonates react with dimethylcyanamide in a [4+2]‐cycloaddition to give 4‐phosphorylated 1,3,5‐oxadiazines. The structures of the products were confirmed by NMR (¹H, ¹³C, ¹⁹F, ³¹P) and IR spectra and by XRD analysis. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:22–26, 2002; DOI 10.1002/hc.1102     

Methyl Trifluoropyruvate Diethoxyphosphorylimine

The first example of trifluoropyruvate phosphorylimines was prepared, and its capability for O- and S-amidoalkylation of water, alcohols, and compounds with the SH function was shown. Phenol and 4-methoxyphenol are O-alkylated, while 3-dimethylaminophenol and indole undergo regiospecific C-alkylation at the site of the highest -electron density.     

N-Acyl-and N-Phosphorylpolyhalogenoalkyl-Imidolylphosphonates: Synthesis and Reactions

Abstract

Methods of synthesis of polyhalogenoalkylimidoyl phosphonates, the phosphorus analogs of a well-known and widely used acylimines of polyhalogenocarbonyl compounds, have been developed.