Electrochemical Oxidation of Polyfluoroalkyl Iodides: Direct Anodic Transformation of C8F17CH2CH2I to Amides, Esters, and Etherst

James Y. Becker, Bruce E. Smart, Tadamichi Fukunaga

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The cyclic voltammetry of polyfluoroalkyl iodides of the type RfCH2CH2I (Rf = n-C6F13, n-C8F17, n-C10F21) and RfI (Rf = n-C4F9, n-C6F13, n-C8F17, n-C10F21) was investigated in nonaqueous media. All the iodides exhibited one distinctive oxidation peak, but only C8F17CH2CH2I was suitable for surveying preparative-scale electrosynthetic reactions because the other iodides either had poor solubility or caused severe filming of the anode. The direct anodic transformations of the iodide to the corresponding amides (C8F17CH2CH2NHCOR; R = CH3, CH=CH2, C(Me)=CH2), esters (C8F17CH2CH2OCOR; R = CH3, CF3, CH=CH2, C(Me)=CH2, C6H5), ethers (mainly C8F17CH2CH2OCH2CF3), and alcohol (C8F17CH2CH2OH) were observed and a general mechanistic scheme involving a hypervalent iodanyl radical intermediate is proposed.

Original languageEnglish
Pages (from-to)5714-5720
Number of pages7
JournalJournal of Organic Chemistry
Issue number24
StatePublished - 1 Nov 1988


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