Unexpected formation of N-fluoroalkaneacyl anilides from the reactions of fluoroalkanesulfonyl azides with nitrobenzene and its derivatives

Unexpected formation of N-fluoroalkaneacyl anilides from the reactions of fluoroalkanesulfonyl azides with nitrobenzene and its derivatives

2011

The thermal reactions of fluoroalkanesulfonyl azides RfCF₂SO₂N₃1 with nitrobenzene and its derivatives XC₆H₄NO₂ (X=H, F, Cl, CF₃) gave the unexpected N-fluoroalkaneacyl anilides RfCONHC₆H₄X (X=H, Cl, F, CF₃) in addition to fluoroalkanesulfonyl amides RfCF₂SO₂NH₂. Under the same reaction conditions, however, nitrobenzene containing an electron-donating group RC₆H₄NO₂ (R=CH₃, OCH₃) reacted with 1 affording the corresponding N-fluoroalkanesulfonyl anilides RfCF₂SO₂NHC₆H₃(NO₂)R. Other electron-poor benzene derivatives, such as benzaldehyde, benzoate, and acetophenone C₆H₅Y(Y=CHO, COCH₃, CO₂CH₃) all gave the meta-substituted N-fluoroalkanesulfonyl anilides RfCF₂SO₂NHC₆H₄Y.

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