The Chemistry of Interhalogen Monofluorides

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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.

Keywords: Alkenes; Markovnikov regiochemistry; aromatic substitutions; cycloheptene; halofluorination; nucleophile ring-opening

Document Type: Research Article

Affiliations: Point Loma Nazarene University, 3900 Lomaland Drive, San Diego, CA 92106, USA.

Publication date: January 1, 2006

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