Documentation scienceplus.abes.fr version Bêta

À propos de : Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation ofQuaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium SaltsLeading to Ionic Liquids        

AttributsValeurs
type
Is Part Of
Subject
Title
  • Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation ofQuaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium SaltsLeading to Ionic Liquids
has manifestation of work
related by
Author
Abstract
  • 1,2,4-Triazole was alkylated (alkyl = methyl, butyl, heptyl, decyl) at N-1 in >90% isolated yields.The resulting 1-alkyl triazoles were quaternized at N-4 in >98% isolated yields using fluorinatedalkyl halides with >98% isolated yields, under neat reaction conditions at 100−120 °C to formN1-CH3-N4-(CH2)2CmF2m + 1-triazolium (Taz) iodide (m = 1, 6), N1-C4H9-N4-(CH2)2CmF2m + 1-Taziodide (m = 1, 4, 6), N1-C7H15-N4-(CH2)2CmF2m + 1-Taz iodide (m = 1, 4, 6), N1-C10H21-N4-(CH2)2CmF2m+1-Taz iodide (m = 1, 4), and N1-CnH2n + 1-N4-(CH2)2F-Taz bromide (n = 4, 7, 10). Single-crystalX-ray analyses confirmed the structure of [1-CH3-4-CH2CH2CF3-Taz]+I-. It crystallized in theorthorhombic space group Pccn, and the unit cell dimensions were a = 13.8289(9) Å, b = 17.3603(11) Å, c = 9.0587(6) Å (α = β = γ = 90°). Metathesis of these polyfluoroalkyl-substituted triazoliumhalides with other salts led to the formation of quaternary compounds, some of which compriseionic liquids, namely, [R(Rf)-Taz]+Y- (Y = NTf2, BF4, PF6, and OTf), in good isolated yields withoutthe need for further purification: N1-CH3-N4-(CH2)2CmF2m +1-Taz Y (m = 1, 6; Y = NTf2), N1-C4H9-N4-(CH2)2CmF2m + 1-Taz Y (m = 1, 4, 6; Y = NTf2), N1- C7H15-N4-(CH2)2CmF2m + 1-Taz Y (m =1, 4, 6; Y = NTf2), N1-C10H21-N4-(CH2)2CmF2m +1-Taz Y (n = 1, 4; Y = NTf2), N1-CnH2n + 1-N4-(CH2)2F-Taz Y (n = 7, 10; Y = NTf2), N1-C10H21-N4-(CH2)2F-TazY (Y = OTf), N1-C7H15-N4-(CH2)2F-TazY (Y = BF4), N1-C4H9-N4-(CH2)2CmF2m+ 1-Taz Y (m = 4, 6; Y = PF6), N1-C7H15-N4-(CH2)2C4F9-Taz Y (Y = PF6), N1-C4H9-N4-(CH2)2CmF2m + 1-Taz Y (m = 4, 6; Y = OTf). All new compounds werecharacterized by 1H, 19F, and 13C NMR and MS spectra and elemental analyses. Tgs and Tms ofionic liquids were determined by DSC.
article type
is part of this journal



Alternative Linked Data Documents: ODE     Content Formats:       RDF       ODATA       Microdata