Trifluoromethanesulfonylimides of arenehydroxamic acids and their aza Lossen rearrangement

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• 作者：Lev M. Yagupolskii ; Svetlana V. Shelyazhenko ; Irina I. Maletina ; Liubov V. Sokolenko ; Alex ; er N. Chernega ; Eduard B. Rusanov ; Ivan F. Tsymbal
• 关键词：Hydroxamic acids ; Rearrangements ; X-ray structure ; Formamidines
• 刊名：Journal of Fluorine Chemistry
• 出版年：2007
• 出版时间：May 2007
• 年：2007
• 卷：128
• 期：5
• 页码：515-523
• 全文大小：569 K

文摘

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 ArNCNSO₂CF₃ 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.