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New fluorinated thiirane derivatives were formed as a result of the reaction between N,N‐disubstituted polyfluoroalkanethioamides and diazomethane. The obtained thiiranes were smoothly desulfurized by the treatment with triphenylphosphine affording 1‐polyfluoroalkyl enamines. New transformations of the synthesized thiiranes and enamines into functionalized 1,4‐dioxanes have been found to occur under...