An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane

Zhang, Cheng‐Pan; Lin, Jin‐Hong; Qiang, Zhenwei; Xiao, Ji‐Chang

doi:10.1002/cjoc.200990019

Cited by 3 publications

(2 citation statements)

References 27 publications

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“…540 An efficient two-step method for the preparation of pentafluoroiodoethane from chloropentafluoroethane was elaborated by Zhang. 534 The treatment of C 2 F 5 Cl with Na 2 S 2 O 4 −NaHCO 3 in DMSO afforded the corresponding fluorinated sulfinate 463a″, which was transformed into C 2 F 5 I by treatment with iodine in 95% yield (Scheme 248). The reaction proceeds through the formation of unstable sulfonyl iodide 466, which extrudes easily SO 2 to give the final product.…”

Section: Reactions Of Pfe With Nucleophilesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

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Section: Reactions Of Pfe With Nucleophilesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

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“…Based on the results described above, an efficient method was found for the synthesis of pentafluoroiodoethane from chloropentafluoroethane using the modified sulfinatodehalogenation reaction (Scheme 67). 79 Sulfinatodechlorination of CF 3 CF 2 Cl (227) with subsequent iodination could be conducted in one pot without further purification to give the CF 3 CF 2 I in an acceptable yield.…”

Section: Modified Sulfinatodehalogenation Reaction -The Discovery App...mentioning

confidence: 99%

Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

et al. 2012

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The sulfinatodehalogenation reaction represents one of the most important methodologies to incorporate fluorine into organic molecules. Using inexpensive sulfur-containing reactants such as Na(2)S(2)O(4) under mild conditions, per- and polyfluoroalkyl halides (R(F)X, X = Br, I, CCl(3)) can be transformed smoothly into the corresponding sulfinate salts. This method is also used for the perfluoroalkylation of alkenes, dienes, alkynes and aromatics. Notably, after 1998, the sulfinatodehalogenation of perfluoroalkyl chlorides (R(F)Cl) has been realized by using dimethylsulfoxide (DMSO) as a solvent instead of CH(3)CN/H(2)O in the Na(2)S(2)O(4)/NaHCO(3) initiation system. Perfluoroalkyl chlorides, ethyl chlorofluoroacetates and chlorodifluoroacetates, and even nonfluorinated compounds, such as ethyl chloro- or dichloroacetates and chloroform, were either converted into the corresponding sulfinate salts or alkylated alkenes, alkynes and aromatics (including porphyrins). The sulfinatodehalogenation reaction has remarkable advantages. With the increasing demands to utilize the unique properties of fluorine and fluorinated functional groups in medicinal, agricultural and material sciences, we believe that there will continue to be useful developments in sulfinatodehalogenation chemistry and it will be applied more widely in the future.

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ChemInform Abstract: An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane.

et al. 2009

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An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane

Cited by 3 publications

References 27 publications

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

ChemInform Abstract: An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane.

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