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Abstract
Oximes, and in particular oximate salts, can be useful nucleophiles for the treatment of organophosphate nerve agent poisoning and decontamination of chemical warfare agents. In this paper, the reactions of phosphonochloridate analogues of the chemical warfare nerve agents VX, GB, and GA and the oximes 2-butanone oxime, 2,3-butanedione monoxime, and its potassium salt (KD), are examined. Under controlled conditions. (0°C, 1 molar eq. KD), the major product is the O-(O-alkyl phosphonyl)oxime; with excess oximate KD, the intermediate phosphonylated oximes containing an α-carbonyl undergo a “second-order” Beckmann rearrangement to give (E)-mono(O-acetyloxime)-2,3-butanedione.
