Hydrolysis of phosphonoformate triesters: Rate acceleration of a millionfold in nucleophilic substitution at phosphorus

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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.

Original languageEnglish (US)
Pages (from-to)793-794
Number of pages2
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
DOIs
StatePublished - 1993
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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