2991-84-6Relevant articles and documents
Moreau et al.
, p. 265 (1975)
New synthesis of polyfluoroalkanesulfonylureas
Benfodda,Delon,Guillen,Blancou
, p. 1353 - 1358 (2008/09/18)
This study describes a new synthesis of F-alkanesulfonyl ureas by reaction of the sodium salt of perfluoroalkane sulfonamide (RF = C4F9, C6F13) with some isocyanates in anhydrous THF. The perfluorinated sulfonylureas are obtained, in one step, from moderate to good yields.
The activation of carbon-chlorine bonds in per- and polyfluoroalkyl chlorides: DMSO-induced hydroperfluoroalkylation of alkenes and alkynes with sodium dithionite
Long, Zheng-Yu,Chen, Qing-Yun
, p. 4775 - 4782 (2007/10/03)
In DMSO, the addition reactions of perfluoroalkyl chlorides, R(F)Cl, to alkenes or alkynes can occur smoothly in the presence of 1.5 equiv of Na2S2O4 and NaHCO3 at 75-80 °C for 4-10 h to give the corresponding adducts (RCH2CH2RF or RCH = CHR(F)). Ethyl chlorofluoro- (1f), chlorodifluoro- (1g) acetates, even nonfluorinated compounds, such as ethyl dichloro- (1h), chloro- (1i) acetates, and chloroform (1j) can undergo the similar reaction. Treatment of ω-iodo (or chloro-) perfluoroalkyl chlorides [X(CF2)(n) Cl, n = 2, 4, X= I or Cl] with > 3 equiv of alkenes and Na2SO4 gives directly the symmetrically disubstituted alkanes (RCH2CH2)2(CF2)(n). The symmetrically and unsymmetrically disubstituted adducts RCH2CH2(CF2)(n)CH2CH2R' from ω-iodoperfluoroalkyl chlorides can be also obtained stepwise, i.e., through the further addition reactions of monoadducts, RCH2CH2(CF2)(n)Cl to olefins. However, for α,ω- dichloroperfluoroalkanes, the similarly stepwise reactions with an alkene is not clean, both bis-adducts and the corresponding ω-hydrides, RCH2CH2(CF2)(n)H as byproducts are also formed. In the absence of alkenes or alkynes, per- and polyfluoroalkyl chlorides can be converted to their sulfinate salts and sulfonyl chlorides.
