2018
DOI: 10.1021/acs.joc.8b02306
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Oxidative Detoxification of Sulfur-Containing Chemical Warfare Agents by Electrophilic Iodine

Abstract: Mild oxidation of sulfur-containing chemical warfare agents was performed in organic medium by electrophilic iodine reagents. Kinetic experiments on sulfur mustard (HD) showed rapid (t 1/2 < 3 min) and selective oxidation to the nonvesicant sulfoxide product (HD-SO) in acetonitrile or propylene carbonate solutions (9% water added) containing excess N-iodosuccinimide (NIS). Molecular iodine solutions in these solvents led to similar results as with NIS but at much slower rates (t 1/2 ∼ 90 min). Higher donor num… Show more

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Cited by 19 publications
(16 citation statements)
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“…Neither the alkyl group on the oxygen (R 2 ) nor the alkyl group on the phosphorous atom (R 1 ) in these compounds contributed notably to the spectrum, and it was difficult to determine the structure of the phosphonate group. For the structural elucidation of the phosphonate group, we employed NIS, which induced the hydrolysis of the V‐nerve agents into their corresponding phosphonic acids 12 …”
Section: Resultsmentioning
confidence: 99%
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“…Neither the alkyl group on the oxygen (R 2 ) nor the alkyl group on the phosphorous atom (R 1 ) in these compounds contributed notably to the spectrum, and it was difficult to determine the structure of the phosphonate group. For the structural elucidation of the phosphonate group, we employed NIS, which induced the hydrolysis of the V‐nerve agents into their corresponding phosphonic acids 12 …”
Section: Resultsmentioning
confidence: 99%
“…Therefore, the development of a selective method for the quantitative degradation of V‐agents to their corresponding alkyl alkylphosphonic acids is highly desirable. Smolkin et al 12 recently developed a mild and selective oxidation of VX nerve agent to nontoxic EMPA with a fast reaction rate ( t 1/2 = 6 min) using an excess of an electrophilic iodine reagent (NIS, 11 equiv) in a DMSO/H 2 O (10:1).…”
Section: Resultsmentioning
confidence: 99%
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“…Oxidation is one of the most important approaches for sulfur‐containing chemical warfare agent (CWA) detoxification, of which a variety of oxidants are available for use 32,33 . Inspired by this chemistry, we sought to use a selective oxidizing agent that converts HD into HDSO, thereby preserving the identity of the HD skeleton, allowing its unambiguous identification via LC‐ESI‐MS/MS analysis.…”
Section: Introductionmentioning
confidence: 99%