Practical and efficient synthesis of perfluoroalkyl iodides from perfluoroalkyl chlorides via modified sulfinatodehalogenation
A novel two-step one pot synthesis of perfluoroalkyl iodides (α,ω-diiodoperfluoroalkanes) from perfluoroalkyl chlorides (α-chloro-ω-iodoperfluoroalkanes) has been developed by initial conversion to the corresponding sodium perfluoroalkanesulfinates with sodium dithionite and then subsequent oxidation by iodine.
Cao, Hai-Ping,Chen, Qing-Yun
p. 1187 - 1190
(2008/02/10)
Redox-Initiated Per(poly)fluoroalkylation of Olefins by Per(poly)fluoroalkyl Chlorides
The per(poly)fluoroalkylation of olefins by per(poly)fluoroalkyl chlorides, initiated by ammonium persulfate/sodium formate ((NH4)2S2O8/HCO2Na), is described.The reaction proceeds smoothly in polar aprotic solvents. The presence of functional groups like sodium carboxylate or sulfonate in the polyfluoroalkyl chloride appear to facilitate the reaction.The reaction appears to be initiated by a single-electron transfer, represents the firat example of the reactivity of per(poly)fluoroalkyl chlorides, and also demonstrates their use as per(poly)fluoroalkylating agents.For α-chloro-ω-iodoperfluoroalkanes only the carbon-iodine bond is cleaved during the reaction.An explantation for the apparent stability of the carbon-chlorine bond in such compounds is given.
Hu, Chang-Ming,Qing, Feng-Ling
p. 6348 - 6351
(2007/10/02)
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