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Synthesis 1993; 1993(7): 693-699
DOI: 10.1055/s-1993-25924
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Poly-4-vinylpyridinium Poly(Hydrogen Fluoride): A Solid Hydrogen Fluoride Equivalent Reagent

George A. Olah* , Xing-Ya Li, Qi Wang, G. K. Surya Prakash
  • *Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA
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Publication Date:
17 September 2002 (online)

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Poly-4-vinylpyridinium poly(hydrogen fluoride) (PVPHF), containing 35-60% hydrogen fluoride by weight, was prepared as a solid hydrogen fluoride equivalent reagent. PVPHF with 60% hydrogen fluoride by weight was found to be a versatile fluorinating agent for the hydrofluorination and bromofluorination of alkenes and alkynes, fluorination of alcohols as well as other fluorination reactions. Low hydrogen fluoride content PVPHF (3 equivalents of hydrogen fluoride to 1 equivalent of 4-vinylpyridine unit) was also found to be an efficient reagent for bromofluorination of alkenes in the presence of 1,3-dibromo-5,5-dimethylhydantoin. Fluorosulfonic acid-modified PVPHF showed enhanced reactivities for the fluorination of secondary alcohols.