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Reactions of Alkyl 1H,1H-Perfluoroalkyl Sulfones with Ammonia, Amines, and Hydrazines

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Abstract

2,2,3,3-Tetrafluoropropyl and 2,2,3,3,4,4,5,5-octafluoropentyl alkyl sulfones react with ammonia, primary and secondary amines, hydrazine hydrate, phenylhydrazine, and N,N-dimethylhydrazine to afford, depending on the length of the polyfluoroalkyl chain and reaction conditions, the corresponding enamines, imines, or mono- and bis-hydrazones. The bis-hydrazone obtained from phenylhydrazine and 2,2,3,3,4,4,5,5-octafluoropentyl benzyl sulfone is capable of undergoing further dehydrofluorination to give 5-difluoromethyl- or 5-unsubstituted 1-phenylpyrazole.

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  1. Ukrainian National Academy of Sciences, Institute of Organic Chemistry, ul. Murmanskaya 5, Kiev, 02094, Ukraine

    V. M. Timoshenko, Ya. V. Nikolin, N. P. Kolesnik & Yu. G. Shermolovich

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  1. V. M. Timoshenko
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  2. Ya. V. Nikolin
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  3. N. P. Kolesnik
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  4. Yu. G. Shermolovich
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Timoshenko, V.M., Nikolin, Y.V., Kolesnik, N.P. et al. Reactions of Alkyl 1H,1H-Perfluoroalkyl Sulfones with Ammonia, Amines, and Hydrazines. Russian Journal of Organic Chemistry 37, 624–632 (2001). https://doi.org/10.1023/A:1012427229154

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  • DOI: https://doi.org/10.1023/A:1012427229154

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