Multi-Gram Scale Synthesis of 1,2,3-Triazolium Ionic Liquids and Assay of Their Resistance towards Bases

被引：11
|
作者：
Raiguel, Stijn [1 ]
Thomas, Joice [1 ]
Binnemans, Koen [1 ]
Dehaen, Wim [1 ]
机构：
[1] Katholieke Univ Leuven, Dept Chem, Celestijnenlaan 200F POB 2404, B-3001 Leuven, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 35期
关键词：
Ionic liquids; Green chemistry; Grignard reaction; Triazolium salts; SOLVENT-EXTRACTION; SALTS; CYCLOADDITION; STABILITY; DATABASE; CATIONS; AZIDES;
D O I：
10.1002/ejoc.201800925
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An easily upscalable synthesis method for 1,2,3-triazolium ionic liquids is presented. Several ionic liquids were synthesized and characterized. The influence of the side chain structure on the base-stability was investigated. One example, functionalized with linear alkyl side chains, was found to exhibit excellent stability against hot concentrated NaOH solutions and Grignard reagents.
引用
收藏
页码：4850 / 4856
页数：7
相关论文
共 50 条
  • [1] Physicochemical properties of 1,2,3-triazolium ionic liquids
    Sanghi, Shilpi
    Willett, Erik
    Versek, Craig
    Tuominen, Mark
    Coughlin, E. Bryan
    RSC ADVANCES, 2012, 2 (03) : 848 - 853
  • [2] Bicyclic 1,2,3-Triazolium Ionic Liquids: Synthesis, Characterization, and Application to Rutaecarpine Synthesis
    Tseng, Ming-Chung
    Cheng, Hui-Ting
    Shen, Meng-Jane
    Chu, Yen-Ho
    ORGANIC LETTERS, 2011, 13 (16) : 4434 - 4437
  • [3] Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids
    Yoshida, Yasushi
    Takizawa, Shinobu
    Sasai, Hiroaki
    TETRAHEDRON LETTERS, 2011, 52 (51) : 6877 - 6879
  • [4] Design and synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids
    Yoshida, Yasushi
    Takizawa, Shinobu
    Sasai, Hiroaki
    TETRAHEDRON-ASYMMETRY, 2012, 23 (11-12) : 843 - 851
  • [5] Biosourced 1,2,3-triazolium ionic liquids derived from isosorbide
    M'sahel, Malek
    Obadia, Mona Marie
    Medimagh, Raouf
    Serghei, Anatoli
    Zina, Mongia Said
    Drockenmuller, Eric
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (01) : 740 - 747
  • [6] Synthesis, characterization, and NMR studies of 1,2,3-triazolium ionic liquids: a good perspective regarding cytotoxicity
    Glanzmann, Nicolas
    Carmo, Arturene M. L.
    Antinarelli, Luciana M. R.
    Coimbra, Elaine S.
    Costa, Luiz Antonio S.
    da Silva, Adilson D.
    JOURNAL OF MOLECULAR MODELING, 2018, 24 (07)
  • [7] Synthesis, characterization, and NMR studies of 1,2,3-triazolium ionic liquids: a good perspective regarding cytotoxicity
    Nicolas Glanzmann
    Arturene M. L. Carmo
    Luciana M. R. Antinarelli
    Elaine S. Coimbra
    Luiz Antônio S. Costa
    Adilson D. da Silva
    Journal of Molecular Modeling, 2018, 24
  • [8] 1-Alkyl-3-methyl-1,2,3-triazolium [NTf2] ionic liquids: synthesis and properties
    Reeder, Zachary K.
    Adler, Abigail M.
    Miller, Kevin M.
    TETRAHEDRON LETTERS, 2016, 57 (02) : 206 - 209
  • [9] Synthesis of 1,3-Dialkyl-1,2,3-triazolium Ionic Liquids and Their Applications to the Baylis-Hillman Reaction
    Jeong, Yunkyung
    Ryu, Jae-Sang
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12): : 4183 - 4191
  • [10] Click synthesis and characterization of 1,2,3-triazolium salts
    Lawal, Nasir S.
    Bala, Muhammad D.
    JOURNAL OF MOLECULAR STRUCTURE, 2020, 1200
12345