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

D. Szabó, János Mohl, Ana Maria Bálint, A. Bodor, J. 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 2006

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synthesis (chemistry)
Amines
amines
tert-Butyl Alcohol
Mechlorethamine
Steam
Butenes
steam
reagents
Display devices
Nitrogen
nitrogen
liquid
Liquids
liquids
amine

Keywords

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

ASJC Scopus subject areas

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

Cite this

Novel generation ponytails in fluorous chemistry : Syntheses of primary, secondary, and tertiary (nonafluoro-tert-butyloxy)ethyl amines. / Szabó, D.; Mohl, János; Bálint, Ana Maria; Bodor, A.; Rábai, J.

In: Journal of Fluorine Chemistry, Vol. 127, No. 11, 11.2006, p. 1496-1504.

Research output: Contribution to journalArticle

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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.",
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N2 - (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.

AB - (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.

KW - Amines

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KW - Steam-distillation

KW - Williamson-synthesis

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