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(R = Me) [59218-87-0] C9H27F2N3SSi (MW 275.55) InChI = 1S/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1 InChIKey = JMGVTLYEFSBAGJ-UHFFFAOYSA-N (R = Et) [59201-86-4] C15H39F2N3SSi (MW 359.73) InChI = 1S/C12H30N3S.C3H9F2Si/c1-7-13(8-2)16(14(9-3)10-4)15(11-5)12-6;1-6(2,3,4)5/h7-12H2,1-6H3;1-3H3/q+1;-1 InChIKey = WRVWLZUYPSYYEW-UHFFFAOYSA-N (anhydrous fluoride ion source; synthesis of CF compounds by nucleophilic displacement of sulfonates;3 promoter for electrophilic reactions of silyl enolates of ketones and esters;4-6 source of sulfonium cation capable of stabilizing or imparting high nucleophilic reactivity to other anions;4, 6, 8a,10a activator of vinylsilanes in Pd-catalyzed cross-coupling reactions;7 also used for generation8 and reactions10 of α- and β-halo carbanions; hydrosilylation11 and cyanomethylation14 of ketones) Alternate Name: TASF. Physical Data: R = Me, mp 98–101 °C; R = Et, mp 90–95 °C. Solubility: R = Me, sol MeCN, pyridine, benzonitrile; partially sol THF. R = Et, sol THF, MeCN. Both react slowly with MeCN. Form Supplied in: R = Me, white crystalline solid, ∼90% pure; major impurity is tris(dimethylamino)sulfonium bifluoride [(Me2N)3S+ HF2−]. Analysis of Reagent Purity: mp; 19F NMR δ (at 200 MHz, CFCl3 standard) TASMe3SiF2 (CD3CN) δ −60.3; TASHF2 −145.8 (d, JHF = 120 Hz). Preparative Methods: the methyl derivative is prepared by the reaction of dimethylaminotrimethylsilane and Sulfur Tetrafluoride at −70 °C to rt in ether; the precipitated solid is filtered off.1a The ethyl derivative is best prepared by the reaction of N,N-Diethylaminosulfur Trifluoride (DAST) and diethylaminotrimethylsilane.1b,11b Handling, Storage, and Precautions: because of the extreme hygroscopic nature of this compound, it is best handled in a dry box or a polyethylene glove bag filled with high purity nitrogen. Use in a fume hood. |
