Journal of the Chemical Society. Perkin transactions II p. 1171 - 1174 (1983)
Update date:2022-08-03
Topics:
Abell, Katherine W. Y.
Kirby, Anthony J.
The dianion (8) of bis-2-carboxyphenyl phosphate (half-life 10.2 min at 39 deg C) is hydrolysed ca. 1E10 times faster than diphenyl phosphate.The reaction is accounted for in terms of intramolecular general acid catalysis by the ortho-CO2H of one salicyl group of the breakdown of the penta-covalent intermediate formed by the addition to phosphorus of the carboxylate group of the other.The general acid catalysis part of the process is unexpectedly inefficient.
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