162308-79-4Relevant academic research and scientific papers
C-F bond substitution via aziridinium ion intermediates
Tr?ff,Janjetovic,Hilmersson
supporting information, p. 13260 - 13263 (2015/08/24)
Aliphatic 1,2-aminofluorides undergo extremely fast substitution reactions under the influence of lanthanum tris(hexamethyldisilazide). The substitution proceeds via an in situ generated aziridinium ion intermediate, which subsequently undergoes ring opening by addition of a nucleophile, yielding various β-substituted amines.
SYNTHESIS OF THREE PARTIALLY FLUORINATED ALKANESULFONIC ACIDS AS POTENTIAL FUEL-CELL ELECTROLYTES.
Bunyagidj,Piotrowska,Aldridge
, p. 344 - 346 (2007/10/02)
The simple and effective syntheses of CH//2FCH//2SO//3H, CF//3CH//2SO//3H, AND CHF//2CF//2CH//2SO//3H have been achieved with 18. 8%, 34. 1%, and 33. 7% overall yields. The low molecuar weight partially fluorinated alkanesulfonic acids containing alpha -methylene groups can be prepared from the p-toluenesulfonates of the corresponding alcohols, via a reaction with benzyl mercaptan, followed by an oxidative chlorination of the resulting sulfides, with subsequent hydrolysis of the sulfonyl chloride. The reaction of partially fluorinated alkyl halides with sodium sulfite (Strecker's method) proved to be inefficient (very low yields) and unreliable. The sulfonate salts formed are difficult to recover and purify.
