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

Csongor Szíjjártó, Peter Ivanko, Ferenc T. Takács, D. Szabó, J. Rábai

Research output: Contribution to journalArticle

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 2008

Fingerprint

dehydroxylation
1-Propanol
Propanol
iodine
distillation
Pyridine
Propanols
pyridines
melt
phosphorus
funnels
Distillation
economy
synthesis
Iodine
Phosphorus
reagents
purity
Atoms
atoms

Keywords

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

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols. / Szíjjártó, Csongor; Ivanko, Peter; Takács, Ferenc T.; Szabó, D.; Rábai, J.

In: Journal of Fluorine Chemistry, Vol. 129, No. 5, 05.2008, p. 386-389.

Research output: Contribution to journalArticle

Szíjjártó, Csongor ; Ivanko, Peter ; Takács, Ferenc T. ; Szabó, D. ; Rábai, J. / Syntheses of fluorous propenes from 3-perfluoroalkyl-2-iodo-1-propanols. In: Journal of Fluorine Chemistry. 2008 ; Vol. 129, No. 5. pp. 386-389.
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