Use of an organometallic palladium ozazoline catalyst for the hydrolysis of methylparathion
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abstract
Reaction of (S)-4-carbomethoxy-2-phenyl-2-oxazoline with Pd(OAc) 2 leads to the formation of the ortho-palladated complex (S,S)-di--(acetate)-bis{2-[2-(4-carbomethoxy)oxazolinyl]phenyl-C,N} dipalladium(II) (1). In the presence of water, this complex reacts with methylparathion to produce p-nitrophenol as well as two oxazoline palladium dimethylthiophosphate complexes (2 and 3), which have been observed in solution by 31P NMR. This reaction is accompanied by racemization of the oxazoline ligand and ultimately produces the dinuclear complex (R,S)-di--(dimethylthiophosphate-S,S)-bis{2-[2-(4-carbomethoxy)oxazolinyl] phenyl-C,N}dipal-ladium(II) (4), which features bridging dimethylthiophosphate ligands. At pH 9-10, complex 1 serves as a precatalyst for the hydrolysis of methylparathion. The reaction rate has a first-order dependence in substrate and palladium catalyst with a second-order rate constant of 726 ( 30) M -1 s -1 at pH 9.0.