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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

Shermolovich Y.; Khyzhan A.; Rusanov E.; Mazepa A.; Rakipov I.; Mykhaylychenko S.

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.

Reaction of N,N-Disubstituted Polyfluoroalkanethioamides with Diazomethane: Entry to New Thiirane Derivatives

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