Hydrolysis of phosphonoformate triesters: rate acceleration of a millionfold in nucleophilic substitution at phosphorus
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 793-794
- https://doi.org/10.1039/p29930000793
Abstract
The base-catalysed hydrolysis of triesters of phosphonoformic acid via P–O bond cleavage proceeds at rates at least 104 times greater than diethyl difluoromethylphosphonate and 106 times greater than diphenyl methylphosphonate. Buffer catalysis and isotope labelling studies suggest the mechanism of rate acceleration by the ethoxycarbonyl group to involve either intramolecular nucleophilic catalyses via a three-membered ring or stereoelectronic assistance, both of which are unprecedented.Keywords
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