- Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): A new, highly efficient difluorocarbene reagent
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TFDA is readily prepared from the reaction of fluorosulfonyldifluoroacetic acid with trimethylsilyl chloride, and it is a very effective and efficient source of difluorocarbene for use in addition reactions to alkenes of a broad scope of reactivities. Acid-sensitive substrates may require an additional purification step involving treatment of the distilled TFDA with sufficient Et3N to remove the acid impurity. Other trialkylsilyl fluorosulfonyldifluoroacetates can also be prepared, and they have been found to have reactivities similar to TFDA. The triethyl derivative, TEFDA is more convenient to prepare in a pure state and has similar reactivity to TFDA. Thus, it may prove to be a superior reagent.
- Dolbier Jr., William R.,Tian, Feng,Duan, Jian-Xin,Li, An-Rong,Ait-Mohand, Samia,Bautista, Olivia,Buathong, Saiwan,Baker, J. Marshall,Crawford, Jen,Anselme, Pauline,Cai, Xiao Hong,Modzelewska, Aneta,Koroniak, Henryk,Battiste, Merle A.,Chen, Qing-Yun
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p. 459 - 469
(2007/10/03)
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- SULFONATION OF F-BUTYL F-VINYLETHER: SYNTHESIS OF A NEW FLUORINATED β-SULTONE AND DERIVATIVES
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The new fluorinated β-sultone, (I) has been prepared from F-butyl F-vinyl ether and sulfur trioxide.It isomerizes to CF3(CF2)3OC(O)Cf2SO2F (II) when heated with sodium fluoride.Two known fluorinated esters, FSO2CF2C(O)OCH3 (III) and CF3(CF2)2C(O)CH3 (IV), have also been synthesized from the reaction of methanol with the β-sultone (I).
- Mohtasham, Javid,Behr, Fred E.,Gard, Gary L.
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p. 349 - 357
(2007/10/02)
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- SILVER (FLUOROSULFONYL)DIFLUOROACETATE - A NEW ROUTE TO FLUOROSULFONYL ESTERS
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New fluorinated esters of the type FSO2CF2C(O)OR and (FSO2CF2C(O)O)2R', (R = CH3, CH3CH2CH2, (CH3)3Si, BrCH2CH2, CH3CH2OC(O)CH2, CH2=CHCH2; R' = CH2, CH2CH2, have been prepared and characterized via the reaction of silver difluoro(fluorosulfonyl)acetate with alkylbromides, alkyliodides, and trimethylsilyl iodide.All new compounds have been characterized by their respective IR/MS/NMR spectra.
- Terjeson, Robin J.,Mohtasham, Javid,Peyton, David H.,Gard, Gary L.
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p. 187 - 200
(2007/10/02)
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