Trifluoromethanesulfonylimides of arenehydroxamic acids and their aza Lossen rearrangement |
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Authors: | Lev M. Yagupolskii Eduard B. Rusanov |
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Affiliation: | Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02660, Murmanskaya Str. 5, Kiev, Ukraine |
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Abstract: | Trifluoromethanesulfonylimides of arenehydroxamic acids ArC( NSO2CF3)NHOH (1), analogues of arenehydroxamic acids, in which sp2 hybridized oxygen atom is replaced by the much stronger electron-withdrawing group NSO2CF3, have been synthesized, and the abilities of these compounds to undergo transformations similar to the Lossen rearrangement have been studied.At heating O-trimethylsilyl or O-tosyl derivatives of acids 1 rearrange to carbodiimides ArN C NSO2CF3 or products of their hydration, the corresponding carbamides. Interaction of acids 1 with sulfinyl chloride or phosphorus pentachloride results in formation of N-trifluoromethylsulfonyl-N′-arenechloroformamidines, ArNHC(Cl) NSO2CF3, which were transformed into their morpholine derivatives and thus characterized. |
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Keywords: | Hydroxamic acids Rearrangements X-ray structure Formamidines |
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