Mixture synthesis of fluorous ketals: Mitsunobu reaction of homologous 3-perfluoroalkyl-propanols with hexafluoroacetone sesquihydrate and collective determination of fluorophilicity values

József Rábai, Ana Maria Bálint, Csongor Szíjjártó, Dénes Szabó

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reaction of hexafluoroacetone sesquihydrate (1, 2 mmol) with a mixture of 3-perfluoroalkyl-propanols (CnF2n+1 (CH 2)3OH; 2a-d: n = 4, 6, 8, 10; 1 mmol each) in an ether solution using the classical Ph3P/diisopropyl azodicarboxylate reagent pair afforded a mixture of ten ketals [(CF3) 2C(O(CH2)3CnF2n+1) 2, 3{a-d} x {a-d}]. The mixture of the ten fluorophilic ketals was easily separated from side products using fluorous extraction (FC-72/CH 3OH). The composition of this fluorous ketal mixture was quantitatively analyzed by GC, and the results obtained were in agreement with predictable trends based on a statistical model. A method for collective fluorophilicity determination of the individual fluorous ketals was supplemented with the calculation of fluorous isotherms and the analysis of gas chromatographic elution orders.

Original languageEnglish
Pages (from-to)761-765
Number of pages5
JournalQSAR and Combinatorial Science
Volume25
Issue number8-9
DOIs
Publication statusPublished - Sep 1 2006

Keywords

  • Combinatorial chemistry
  • Elution order
  • Fluorophilicity
  • Gas chromatography
  • Synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Computer Science Applications
  • Organic Chemistry

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