Diethylphosphonoacetic acid

Description

Diethylphosphonoacetic Acid (DPA) is a Horner-Wadsworth-Emmons (HWE) reagent. The mixed anhydride of trifluoroacetic acid—diethylphosphonoacetic acid Treat a 21-hydroxy-20-keto steroid leads directly to cardenolides by an intramolecular Horner-Emmons reaction. It could also used as a dummy template to prepare a molecularly imprinted polymer  for use as an artificial receptor for organophosphorus pesticides (OPPs)[1-3].

Chemical properties

clear colorless to yellow viscous liquid

The Uses of Diethylphosphonoacetic acid

Diethylphosphonoacetic Acid is a reagent that is used for enantioselective preparation of α-phosphoryl-α,β-unsatd.-δ-aryl-δ-lactones from nonracemic β-hydroxyaldehydes and their conversion to α-methylene-δ-aryl-δ-lactones.

The Uses of Diethylphosphonoacetic acid

Acts as a nucleophile for nucleophilic addition reactions for synthesis of allene epoxides

Reactant for:

• Stereoselectivity studies of the Staudinger reaction
• Enantioselective formation of diols via epoxidation and hydration reactions
• Horner-Wadsworth-Emmons reactions
• Remote chelation controlled Ireland-Claisen rearrangement
• Ugi-Dieckmann reactions for synthesis of tetramic acid derivatives

What are the applications of Application

Diethylphosphonoacetic acid is a nucleophile for nucleophilic addition reactions

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 4534, 1980 DOI: 10.1021/ja00533a047

References

[1] S. Donovan, J. Mcmurry, M. Avery. “Synthesis of digitoxigenin by remote functionalization.” Tetrahedron Letters 20 1 (1979): 3287–3290.
[2] A. M. Boldi, Hisham O. Eissa, Charles R. Johnson. “Solid-phase library synthesis of triazolopyridazines via [4+2] cycloadditions.” Tetrahedron Letters 40 1 (1999): 619–622.
[3] Lu Zhang. “Preparation and Characterization of Broad-Spectrum Artificial Antibody for OPPs Based on Dummy Template Imprinting Technique.” International Journal of Polymer Analysis and Characterization 117 1 (2014): 510–521.