N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

LM Yagupolskii, II Maletina, LV Sokolenko…

Index: Yagupolskii, Lev M.; Maletina, Irina I.; Sokolenko, Liubov V.; Vlasenko, Yurii G.; Buth, Sergey A. Journal of Fluorine Chemistry, 2008 , vol. 129, # 6 p. 486 - 492

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Citation Number: 7

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 ...