No abstract

Interhalogen fluorides (XF; X = I, Br, or Cl) generated from xenon difluoride (XeF2) or triethylamine trihydrofluoride (TREAT HF) with iodine (I2), N-halosuccinimides (NXS; X = I, Br, or Cl), or alkylhypohalites (ROX; R = CH3 or t-Bu, X = Br or Cl) with alkenes and aromatics are reported. A comparison of the above reactions with other methods reported in the literature to generate interhalogen fluorides is made. Interhalogens generated from direct action of elemental fluorine (F2) or XF3 (X = I, Br, or Cl) with chlorine (Cl2), bromine (Br2), or iodine (I2) give a species that can react with electron-deficient alkenes or aromatics. These reagents are too reactive for electron-rich substrates. Interhalogen fluorides from reagents like NXS or ROX with XeF2 or amine HF are much less reactive and give good yields with electron-rich akenes or aromatics.

Iodine monofluoride, generated from XeF 2 and I 2 or NIS, reacts with alkenes to furnish iodofluorinated products [cf. (II), (IV), (V)] in good yields. The reaction of aromatics with XeF 2 and I 2 or NIS proceeds as electrophilic aromatic iodination [→ (VII), (IX)]. Iodine monofluoride (IF), generated from XeF 2 proves to be less reactive than IF generated from I 2 and fluorine gas. -(SHELLHAMER, D. F.; JONES, B. C.; PETTUS, B. J.; PETTUS, T. L.; STRINGER, J. M.; HEASLEY, V. L.; J.