SYNTHESIS OF NEW FRAMEWORK PHOSPHONATES BY THE INTERACTION OF 2-ETHOXYVINYL DICHLOROPHOSPHONATE WITH 4-ETHYLRESORCINOL

Abstract

A simple, new and promising approach to obtaining previously unknown phosphorus-containing framework compounds by the developed original synthesis method is proposed. The proposed method is based on the condensation reaction of 2-ethoxyvinylphosphonic acid dichloride with resorcinol and its derivatives in toluene in the presence of trifluoroacetic acid. The article presents the results of a study of the reaction of 2-ethoxyvinyl dichlorophosphonate with 4-ethylresorcinol. It was found that this reaction results in the formation of a mixture of two regioisomers. The structure and construction of the obtained regioisomeric framework phosphonates were studied using ³¹P and ¹H NMR. The regioisomeric framework phosphonates obtained as a result of the reaction of vinylphosphonate with 4-ethylresorcinol were separated by acylation of the mixture with acetic anhydride, using as a medium and a reagent. One functionalized regioisomer was isolated as an individual product, which was white crystals with good solubility in acetone-water and DMSO mixtures. The structure and composition of the obtained regioisomer were confirmed by ¹H, ³¹P, ¹³C NMR, IR spectroscopy, mass spectrometry (MALDI) and elemental analysis. It was found that the reaction of 2-ethoxyvinyl dichlorophosphonate with 4-ethylresorcinol in the presence of an equimolar amount of trifluoroacetic acid in toluene resulted in the formation of a regioisomeric mixture of framework phosphonates in a 4:1 ratio. It was shown that acylation of this regioisomeric mixture with acetic anhydride allowed one of the regioisomers to be isolated individually.