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Abstract
The reaction of aryl β-chloroethyl ketones with triethyl phosphite to give γ-ketophosphonates was studied kinetically. This reaction follows a second order overall and involves a carbonyl group-assisted (CGA) initializing step, followed by a stereoselective pathway to γ-ketophosphonates. A linear Hammett plot reveals that the p value is 1.51 (r=0.994), and the transition state is accelerated by the para- halogen on the phenyl group. The results confirm the two-stage mechanism and rule out an SN2 mechanism being responsible for the formation of diethyl 3-oxo-3-arylpropyl phosphonates 3.