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Synthesis 1987; 1987(10): 920-921
DOI: 10.1055/s-1987-28123
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Use of Polyethylene Glycol in the Synthesis of Alkyl Fluorides from Alkyl Sulfonates

Domenico Badone* , Giancarlo Jommi, Roberto Pagliarin, Paolo Tavecchia
  • *Dipartimento Chimica Organica ed Industriale, Facoltà di Scienze, Universitá degli Studi di Milano, via G. Venezian, 21, I-20133 Milano, Italy
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Publication Date:
12 September 2002 (online)

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In the synthesis of monoflourinated organic compounds, the reaction of potassium fluoride with mesylates and tosylates of alcohols affords fluoro derivatives when polyethylene glycol 400 is used as solvent and catalyst. The limitation of this reaction is the solvolysis of the leaving group by the solvent; the phenomenon is controlled by the degree of steric hindrance around the reaction centre.