Generation of Interhalogen Fluorides under Mild Conditions:  A Comparison of Sluggish and Reactive Interhalogen Fluorides

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 comparis...

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Veröffentlicht in:Journal of organic chemistry 1999-02, Vol.64 (4), p.1094-1098
Hauptverfasser: Shellhamer, Dale F, Horney, Mark J, Pettus, Benjamin J, Pettus, Tobiah L, Stringer, Joy Merry, Heasley, Victor L, Syvret, Robert G, Dobrolsky, John M
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo972319g