Intramolecular Monodealkylation During the Attempted Synthesis of Diethylphosphonoacetohydroxamic Acid.

Abstract

Organo-phosphorus compoundsOrgano-phosphorus compounds S 0080 Intramolecular Monodealkylation During the Attempted Synthesis of Diethylphosphonoacetohydroxamic Acid. -Attempts to obtain the diethylphosphonoacetohydroxamic acid (II) by reaction of diethyl phosphonoacetate (I) with hydroxylamine in alkaline medium result in the unexpected formation of monoethylphosphonoacetohydroxamic acid (III) as the major product. The unexpected monodealkylation is interpreted in terms of an intramolecular nucleophilic catalysis by the hydroxamic OH group attacking the phosphorus atom in (II). -(CHEN, R.; BREUER*, E.; Heteroat.