The preparation and characterization of 2-propylphosphinediacetic acid

Abstract

Phosphineacetic acids of the RP(CH2COOH)2 type, where R is a large substituent with a +I-effect, cannot be prepared by the reaction of chlorophosphine with an organozinc compound because of the lability of the P-CH2COO bonds. The bis(ethyl ester) of 2-propylphosphinediacetic acid as the simplest substance of this kind was prepared by the reaction of chlorophosphine with ethylacetate enolate, which is universal for these substituents. 2-Propylphosphinediacetic acid, obtained from the ester by the usual procedure, was characterized with respect to its use as a hydrophilic phosphine ligand.