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2 protocols using benzyl 2 2 2 trichloroacetimidate

1

Extraction and Analysis of Organophosphorus Compounds

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All chemicals were purchased from commercial suppliers and used as received, ethyl methylphosphonic acid (EMPA), cyclohexyl methylphosphonic acid (CMPA), pinacolyl methylphosphonic acid (PMPA), benzyl 2,2,2-trichloroacetimidate, 4-methoxybenzyl-2,2,2-trichloroacetimidate, acetonitrile (ACN), acetone, ethyl acetate and dichloromethane were purchased from Sigma-Aldrich (St. Louis, MO.). Sodium bicarbonate, sodium carbonate and anhydrous sodium sulfate were purchased from Acros Organics (Westchester, PA). Deuterated chloroform (CDCl3) was purchased from Alfa Aesar (Ward Hill, MA). Acrodisc PTFE syringe filters (0.45 μm) were purchased from Pall laboratories (Port Washington, NY.). Autosampler vials and glass inserts were purchased from Agilent Technologies (Santa Clara, CA.). Soil sample PT-S2 and liquid matrix CW-O3 were obtained from the Forensic Science Center (FSC) OPCW-PT sample archives at the Lawrence Livermore National Laboratory (LLNL).
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2

Levoglucosenone Synthesis and Derivatization

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Chemical and reagents. All manipulations with air-sensitive chemicals and reagents were performed using standard Schlenk techniques on a dual-manifold line, on a high-vacuum line. Levoglucosenone was graciously provided by Circa group. Potassium carbonate 99% (Acros), cesium carbonate 99.5% (Acros), hydrogen peroxide 30% (Fischer). Isosorbide, palladium on carbon (10%), aqueous hydrochloric acid (36% w/w), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (98%), benzyl 2,2,2trichloroacetimidate (99%) and dimethyl carbonate (99%) were purchased from Sigma-Aldrich. HPLC grade solvents (dimethylformamide, ethyl acetate, methanol, dichloromethane and cyclohexane) were purchased from Thermofisher Scientific and used as received. Ultra-pure laboratorygrade water was obtained from MilliQ,18.2 megaOhms. TLC analyses were performed on an aluminum strip coated with Silica Gel 60 F254 from Merck, revealed under UV-light (254 nm) then in presence of potassium permanganate staining solution. All chemicals and reagents were used as received without purification.
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