Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols

Csongor Szíjjártó, Peter Ivanko, Ferenc T. Takács, Dénes Szabó, József Rábai

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2 Citations (Scopus)

Abstract

3-(Perfluoroalkyl)-1-propenes are obtained in excellent yields up to 100-g quantities by deiodination-dehydroxylation reactions of the easily accessible 2-iodo-3-(perfluoroalkyl)-propanols with red phosphorus and catalytic amounts of iodine or with an SnCl2/POCl3 reagent pair in pyridine (fluorous Cornforth reaction). Both methods afford fluorous propenes in high GC purity, the former one has high atom-economy and proceeds safely if the fluorous iodohydrin precursors are added in increments; for the solid ones using a 'hot-melt' dropping funnel. The title fluorous propenes are effectively isolated by co-distillation with pyridine.

Original languageEnglish
Pages (from-to)386-389
Number of pages4
JournalJournal of Fluorine Chemistry
Volume129
Issue number5
DOIs
Publication statusPublished - May 1 2008

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Keywords

  • Atom-economy
  • Fluorine
  • Fluorous distillation
  • Liquid-liquid phase separation
  • Propenes

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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