Reaction of N,N-Disubstituted Polyfluoroalkanethioamides with Diazomethane: Entry to New Thiirane Derivatives
Eur. J. Org. Chem. 2021, 2021 (47), 6524-6529
DOI: 10.1002/ejoc.202001104
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 the action of m-chloroperoxybenzoic acid. The structures of 1,4-dioxanes containing trifluoromethyl and pentafluoroethyl groups have been determined by X-ray diffraction analysis.