Interhalogen monofluorides (XF; X=Cl, Br or I) generated in situ from hypohalites or N-halosuccinimides and a source of fluoride ion are “sluggish” electrophiles. XF reagents formed from F2 gas and a halogen source (ie: ClF3, Br2, I2,) are very reactive electrophiles. This wide range of reactivity allows the synthetic chemist to carry out reactions on electron-rich or electron-deficient substrates. Halofluorinations of alkenes, alkynes and electrophilic aromatic substitution without catalyst are reviewed. Synthesis of geminal difluorides from hydrazones is also presented.
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Cite this chapter as:Dale F. Shellhamer, Victor L. Heasley ;
The Chemistry of Interhalogen Monofluorides, Advances in Organic Synthesis Modern Organofluorine Chemistry-Synthetic Aspects (2006) 2: 43. https://doi.org/10.2174/978160805198410602010043
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