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Title: Aprotic Heterocyclic Anion Triazolide Ionic Liquids - A New Class of Ionic Liquid Anion Accessed by the Huisgen Cycloaddition Reaction

Abstract

The triazole core is a highly versatile heterocyclic ring which can be accessed easily with the Cu(I)-catalyzed Huisgen cycloaddition reaction. Herein we present the preparation of ionic liquids that incorporate a 1,2,3-triazolide anion. These ionic liquids were prepared by a facile procedure utilizing a base-labile pivaloylmethyl group at the 1-position, which can act as precursors to 1H- 4-substituted 1,2,3-triazole. These triazoles were then subsequently converted into ionic liquids after deprotonation using an appropriate ionic liquid cation hydroxide. The densities and thermal decompositions of these ionic liquids were measured. These novel ionic liquids have potential applications in gas separations and in metal-free catalysis.

Authors:
 [1];  [2];  [1];  [1]
  1. National Energy Technology Laboratory
  2. Department of Chemistry, University of Pittsburgh
Publication Date:
Research Org.:
National Energy Technology Lab. (NETL), Albany, OR (United States)
Sponsoring Org.:
USDOE Office of Fossil Energy (FE)
OSTI Identifier:
1129490
Report Number(s):
A-CONTR-PUB-009
Journal ID: ISSN 0936-5214
DOE Contract Number:  
FE0004000
Resource Type:
Journal Article
Journal Name:
Synlett
Additional Journal Information:
Journal Volume: 24; Journal Issue: 09; Journal ID: ISSN 0936-5214
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; ionic liquids; triazoles; triazolides; aprotic; heterocyclic anions; CO2 capture; click chemistry

Citation Formats

Thompson, Robert, Damodaran, Krishnan, Luebke, David, and Nulwala, Hunaid. Aprotic Heterocyclic Anion Triazolide Ionic Liquids - A New Class of Ionic Liquid Anion Accessed by the Huisgen Cycloaddition Reaction. United States: N. p., 2013. Web. doi:10.1055/s-0033-1338435.
Thompson, Robert, Damodaran, Krishnan, Luebke, David, & Nulwala, Hunaid. Aprotic Heterocyclic Anion Triazolide Ionic Liquids - A New Class of Ionic Liquid Anion Accessed by the Huisgen Cycloaddition Reaction. United States. https://doi.org/10.1055/s-0033-1338435
Thompson, Robert, Damodaran, Krishnan, Luebke, David, and Nulwala, Hunaid. 2013. "Aprotic Heterocyclic Anion Triazolide Ionic Liquids - A New Class of Ionic Liquid Anion Accessed by the Huisgen Cycloaddition Reaction". United States. https://doi.org/10.1055/s-0033-1338435. https://www.osti.gov/servlets/purl/1129490.
@article{osti_1129490,
title = {Aprotic Heterocyclic Anion Triazolide Ionic Liquids - A New Class of Ionic Liquid Anion Accessed by the Huisgen Cycloaddition Reaction},
author = {Thompson, Robert and Damodaran, Krishnan and Luebke, David and Nulwala, Hunaid},
abstractNote = {The triazole core is a highly versatile heterocyclic ring which can be accessed easily with the Cu(I)-catalyzed Huisgen cycloaddition reaction. Herein we present the preparation of ionic liquids that incorporate a 1,2,3-triazolide anion. These ionic liquids were prepared by a facile procedure utilizing a base-labile pivaloylmethyl group at the 1-position, which can act as precursors to 1H- 4-substituted 1,2,3-triazole. These triazoles were then subsequently converted into ionic liquids after deprotonation using an appropriate ionic liquid cation hydroxide. The densities and thermal decompositions of these ionic liquids were measured. These novel ionic liquids have potential applications in gas separations and in metal-free catalysis.},
doi = {10.1055/s-0033-1338435},
url = {https://www.osti.gov/biblio/1129490}, journal = {Synlett},
issn = {0936-5214},
number = 09,
volume = 24,
place = {United States},
year = {2013},
month = {4}
}