Fukuto_1959_J.Am.Chem.Soc_81_372

Reference

Title : The Effect of Structure on the Reactivity of Alkylphosphonate Esters - Fukuto_1959_J.Am.Chem.Soc_81_372
Author(s) : Fukuto TR , Metcalf RL
Ref : Journal of the American Chemical Society' , 81 :372 , 1959
Abstract :

A number of new ethyl p-nitrophenyl alkylphosphonates were prepared and the effect of the alkyl moiety on the lability of the phosphorus-0-p-nitrophenyl bond as measured by alkaline hydrolysis was examined. It was found that the rate of hydrolysis of these alkylphosphonates to p-nitrophenol and ethyl alkylphosphonic acid, in general, decreased with increase in alkyl chain length. Compared to the straight chain compounds, branching in the 1- and 2- positions greatly decreased the hydrolysis rate. The rate of reaction of these compounds with insect cholinesterase also was measured and compared with the hydrolysis rate. Many of these compounds showed high toxicity to the common housefly, Musca domestica L., and degree of toxicity was parallel to cholinesterase inhibition.

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Fukuto TR, Metcalf RL (1959)
The Effect of Structure on the Reactivity of Alkylphosphonate Esters
Journal of the American Chemical Society' 81 :372

Fukuto TR, Metcalf RL (1959)
Journal of the American Chemical Society' 81 :372