N-Fluorobenzenesulfonimide Synthesis Essay


InChI = 1S/C12H10FNO4S2/c13-14(19(15,16)11-7-3-1-4-8-11)20(17,18)12-9-5-2-6-10-12/h1-10H


(electrophilic fluorinating agent)

Alternative Names:N-fluorobenzenesulfonimide; N-fluorobis(phenylsulfonyl)amine; N-fluorodibenzenesulfonimide, NFSi.

Physical Data: mp 114–116 °C.

Solubility: sol various organic solvents, including THF (0.24 gml−1), CH2Cl2 (0.40 gml–1), acetonitrile (0.25 gml−1), and toluene (0.09 gml−1).

Form Supplied in: white or slightly yellow solid, >98% purity; commercially available.

Analysis of Reagent Purity:1H and 19F NMR.

Preparative Method: pressureless fluorination on a 0.2 mol scale with F2 in N2 (F2/N2 10% v/v) in the presence of powdered NaF in acetonitrile at −40 °C.1

Purification: flash chromatography (SiO2, CH2Cl2) and/or crystallization from Et2O.

Handling, Storage, and Precautions: handle and store at rt or below; protected from light, preferably under nitrogen or argon. Thermally stable up to 180 °C; decomposes exothermally at higher temperatures. Reacts with easily oxidized compounds such as iodide. This reagent should be handled in a fume hood.

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