SYNTHESIS, NMR CHARACTERIZATION AND FAB-MS SPECTRA OF SOME ARYLMETHYL-AMINO-PHOSPHONIC ACID MONOETHYL ESTERS

Abstract

Substituted arylmethyl-amino-phosphonic acid monoethyl esters have been synthetized by alkaline hydrolysis of the parent diester derivatives. Diastereoisomerizations due to racemization at the chiral ─CH─ centers were observed in the hydrolytic process. Our compounds are very soluble in water and strong polar organic solvents; therefore, these derivatives can be used for biological and agrochemical tests in hydrophilic media. Some of the prepared compounds are deeply coloured and their absorption maxima are pH-dependent. The ¹H and ³¹P-NMR spectra show interesting features, whereas the MSFAB obtained with negative ion source are diagnostic for structural assignments. In all MS spectra, peaks due to cluster ions [nM ‐ Na]⁻ where observed.

Key Words:

• Water soluble phosphonic acid monoethyl esters
• synthetic procedure
• racemization
• U.V., NMR
• MS spectroscopic properties
• dyes