Mechanism of nucleophilic displacement at phosphorus in the alkaline hydrolysis of phosphinate esters

RD Cook, CE Diebert, W Schwarz…

Index: Cook,R.D. et al. Journal of the American Chemical Society, 1973 , vol. 95, p. 8088 - 8096

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Citation Number: 46

Abstract

Abstract: dimethoxyethane-water or 33 dioxane-water. Rates are second order: u= k [ester][HO-1. Oxygen-18 experiments demonstrate that hydroxide attack occurs only at phosphorus and that the phosphinyl oxygen does not exchange l80 with solvent during hydrolysis. Activation enthalpies ranged from 12 to 16 kcal/mol, and activation entropies were near-30 gibbs. A comparison of rates foI the strained, cyclic 2, 2, 3, 4, 4- ...

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