Novel generation ponytails in fluorous chemistry: Syntheses of primary, secondary, and tertiary (nonafluoro-tert-butyloxy)ethyl amines

Dénes Szabó, János Mohl, Ana Maria Bálint, Andrea Bodor, József Rábai

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

(Nonafluoro-tert-butyloxy)ethyl tosylate 4 was prepared in 65% yield from nonafluoro-tert-butanol 1 using commercially available reagents. Further reaction of 4 with HNR1R2 (R1 = R2 = H, CH3; R1 = H, R2 = CH3, (CH2)3C8F17, CH2CH2OC(CF3)3) affords the appropriate (CF3)3COCH2CH2NR1R2 amines in 20-69% yields. Improved overall yields of [(CF3)3COCH2CH2]3-nNRn to 1 were obtained by the reaction of (CF3)3CONa 2 and (XCH2CH2)3-nNRn (X = Cl, n = 0, 1, 2, R = CH3; X = CH3SO2O, n = 1, R = CH3SO2) nitrogen mustards and a similar reactive β-substituted ethyl amine. The title amines are mobile colorless liquids and volatile with steam. The bulky fluorous ponytail (CF3)3CO(CH2)2 displays high acidic stability and increases fluorous character almost as much as the classical straight-chain C8F17(CH2)3 ponytail.

Original languageEnglish
Pages (from-to)1496-1504
Number of pages9
JournalJournal of Fluorine Chemistry
Volume127
Issue number11
DOIs
Publication statusPublished - Nov 1 2006

Keywords

  • Amines
  • Ethers
  • Fluorous partition coefficient
  • Steam-distillation
  • Williamson-synthesis

ASJC Scopus subject areas

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

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