Supriya Ghosh (Editor)

TASF reagent

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Appearance
  
Colorless solid

Chemical formula
  
C9H27F2N3SSi

Pubchem
  
9795567

TASF reagent httpsuploadwikimediaorgwikipediacommonsthu

The TASF reagent or tris(dimethylamino)sulfonium difluorotrimethylsilicate is a reagent in organic chemistry with structural formula [((CH3)2N)3S]+[F2Si(CH3)3]. It is an anhydrous source of fluoride and is used to cleave silyl ether protective groups. Many other fluoride reagents are known, but few are truly anhydrous, because of the extraordinary basicity of "naked" F. In TASF, the fluoride is masked as an adduct with the weak Lewis acid trimethylsilylfluoride (FSi(CH3)3). The sulfonium cation ((CH3)2N)3S+ is unusually non-electrophilic due to the electron-donating properties of the three (CH3)2N substituents.

This compound is prepared from sulfur tetrafluoride:

3 (CH3)2NSi(CH3)3 + SF4 → 2 (CH3)3SiF + [((CH3)2N)3S]+[F2Si(CH3)3]

The colorless salt precipitates from the reaction solvent, diethyl ether.

References

TASF reagent Wikipedia


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