TY - JOUR
T1 - Hydrolysis of phosphonoformate triesters
T2 - Rate acceleration of a millionfold in nucleophilic substitution at phosphorus
AU - Krol, E. S.
AU - Thatcher, Gregory R.J.
PY - 1993
Y1 - 1993
N2 - 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.
AB - 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.
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U2 - 10.1039/p29930000793
DO - 10.1039/p29930000793
M3 - Article
AN - SCOPUS:37049068350
SN - 1472-779X
SP - 793
EP - 794
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 5
ER -