Novel synthesis of α-acetylstyrylphosphonates

Article abstract of DOI:10.1055/s-1993-25926

α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (animals). 4-Benzylidenemorpholinium carboxylates, generated from animals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.