Journal of Organic Chemistry p. 347 - 354 (1983)
Update date:2022-08-03
Topics:
Feiring, Andrew E.
The reaction of primary perfluoroalkyl iodides (RfI, Rf = n-C6F13, n-C8F17) and diiodides I(CF2)nI (n=4,6) with the 2-nitropropyl anion gives 2-(perfluoroalkyl)-2-nitropropanes.The anion was employed as the tetrabutylammonium salt in benzene or in organic solvent /water mixtures or as the lithium salt in dimethylformamide or dimethyl sulfoxide with and without UV irradiation.Evidence is presented for an SRN1 process by trapping of radical intermediates with benzene, styrene, methyl methacrylate, and vinyl acetate and by competition experiments with p-dinitrobenzene.Substitution of the nitro group in the 2-(perfluoroalkyl)-2-nitropropanes occurs under SRN1 conditions with 2-nitropropyl anion, benzenethiolate, and hydride.
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