Fragmentation of methyl hydrogen α-hydroxyiminobenzylphosphonates—kinetics, mechanism and the question of metaphosphate formation

J Katzhendler, H Schneider, R Ta-Shma…

Index: Katzhendler, Jehoshua; Schneider, Hava; Ta-Shma, Rachel; Breuer, Eli Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 9 p. 1961 - 1968

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Abstract

The thermodynamics, pH dependency and solvent effects of the fragmentation reaction of a series of α-oxyiminobenzylphosphonate monomethyl esters [(E)-1a–f] were examined in water and other hydroxylic solvents by UV and by 31P NMR spectroscopy at pH 0–3.1. The fragmentation of compounds (E)-1a–f was found to be a first-order reaction in substrate over the acidity range studied, while the dependence on the acidity is more complex, with rate ...