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- W2953288212 abstract "The reaction of diethyl methyl phosphonoacetate (1) with hydroxylamine in NaOH solution resulted in the loss of one of the phosphorus ethyl groups, and yielded monoethylphosphonoacetohydroxamic acid (2) as the major product (79%) and diethylphosphonoacetic acid (3) as the minor product (21%). A series of control experiments were carried out to elucidate the sequence of the reactions leading to 2. When the reaction of 1 with NH2OH was carried out in NaHCO3 solution, a transient product 4 was also observed, which slowly transformed to 2. Compound 4 was assigned the structure diethylphosphonoacetohydroxamic acid. There was no dealkylation observed at the phosphorus when 1 was reacted with methoxylamine or when O-methyl diethylphosphonoacetohydroxamate (7) was placed in alkaline solution. The dealkylation at phosphorus was interpreted in terms of intramolecular nucleophilic catalysis by the hydroxamic OH group attacking the phosphorus in 4, involving cyclic 1,2,5-oxazaphospholidine intermediates. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:67–71, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10082" @default.
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- W2953288212 date "2003-01-01" @default.
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- W2953288212 title "Intramolecular monodealkylation during the attempted synthesis of diethylphosphonoacetohydroxamic acid" @default.
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- W2953288212 doi "https://doi.org/10.1002/hc.10082" @default.
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