Triazolium-based ionic liquid

K. Damodaran, X. Zhou, M. Haranczyk, E. Albenze, D.R. Luebke, D. Hopkinson, J.B. Kortright, H.B. Nulwala, Branched isomeric 1,2,3-triazolium-based ionic liquids new insight into structure—property relationships, Phys. Chem. Chem. Phys. 17 (44) (2015) 29834-29843. 

J.J. AUen, Y. Schneider, B.W. Kad, D.R. Luebke, H. Nulwala, K. Damodaran, Nuclear spin relaxation and molecular interactions of a novel triazolium-based ionic liquid, J. Phys. Chem. B 117 (14) (2013) 3877-3883. 

Study of Some Thermophysical and Transport Properties of Triazolium-Based Ionic Liquids. 

Most of the 1,2,3-triazolium based ionic liquids are room temperature ionic liquids (RTILs) (Fletcher, Keeney et al. 2010 Khan, Hanelt et al. 2009). So far, not so many physical constants have been reported. Viscosity measurements and differential thermogravimetry (TGA) measurements of some 1,3,4-trisubstituted 1,2,3-triazolium ionic liquids counter-ions Qeong and Ryu 2010 Khan, Hanelt et al. 2009). These reports indicated good thermal stability up to 355 °C, which is strongly dependent on several variables such as the kind of counter-ion and the nature of substituents on the triazolium ring. One can tune the stability of 1,2,3-... 

Figure 20.4 shows some five-membered cations including imidazolium, pyrazolium, triazolium, thiazolium, and oxazolium. Recently, Siriwardana et al. introduced methimazolium-based ionic liquids as a good coordinating solvent... 

Recently, the ability of N-heterocyclic carbenes to promote the Staudinger reaction has been investigated using ionic liquids, in the presence of suitable base as pre-catalysts. According to the procedure suggested by Smith et al., a solution of base (potassium hexamethyldisilazide KHMDS, toluene as solvent) was added to the suspension of ionic liquid (triazolium salt) in Et O and stirred under N. Subsequently, the mixture was added of diphenylketene and of imine and stirred at room temperature before concentration in vacuo (Scheme 16.6). The order of addition of reactants is critical for the success of the synthesis [95]. 

In addition to traditional organocatalysis, ionic liquids as new catalytic systems have been explored. The first examples used nonimmobilised OTBDPS-L-Ser, protonated arginine or lysine in the presence of ionic liquids based on l-alkyl-3-methyl imidazolium ([bmim], [hmim], [omim]) or JV-butyl-N-methyl pyrrolidinium ([bmpy]) ions. The systems, in addition to giving the aldol adducts with high yields and ee, are efficient for catalyst recovery and reuse. Since 2010 new structures containing a primary amino acid coupled with a 1,2,3-triazolium salt, an acyl group or a polystyrene have been developed. The more effective ones for the aldol reaction depicted Scheme 12.3 (13, 14 and 15, respectively) are represented in Figure 12.3. 

Schaller, U. (2011) Triazolium based energetic ionic liquids. 8th Workshop on Pyrotechnic Combustion, Reims, France, May 14. 

Chowdhury, A., Thynell, S. T. Wang, S. (2009b). Ignition Behavior of Novel Hyp>ergolic Materials, AMA Paper 2009-5352, ISSN 0146-3705 Chowdhury, A. Thynell, S. T. (2010a). Confined rapid thermolysis/FTIR/ToF studies of methyl-amino-triazolium-based energetic ionic liquids, Thermochim. Acta, Vol. 505,... 

Glucose-linked 1,2,3-triazolium ionic liquid 122 was prepared by copper(I)-catalyzed regioselective cycloaddition of a glucose azide with a glucose alkyne followed by quaternization with methyl iodide (Scheme 6.32). This IL was used as reusable ligand and solvent in copper(I)-catalyzed amination of aryl hahdes with aqueous ammonia [71]. Similar chemistry, that is, chcking of P-propargylxyloside with phenyl azide, followed by acetate removal and methylation was employed for the syntheses of D-xylose-based ionic hquids [72]. 

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