N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement |
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Authors: | Lev M Yagupolskii Sergey A Buth |
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Institution: | Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02094 Murmanskaya, Str. 5, Kiev, Ukraine |
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Abstract: | The analogues of carboxamides in which the sp2-hybridized oxygen atom is replaced by more electron-withdrawing groups, NSO2CF3 and NSO2C4F9, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC(NSO2Rf)NH2 (Rf = CF3, C4F9) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArNCNSO2Rf under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC(NSO2R)NH2 (R = CH3, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R. |
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Keywords: | Amidines Rearrangements X-ray structure Carbodiimides |
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