β-Cyclodextrin conjugated imidazolium cation: A neutral, eco-friendly and water-miscible dicationic ionic liquid in the regioselective ring opening of epoxides

Authors

  • Ali Reza Kiasat Department of Chemistry, College of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran.
  • Fatemeh Moheiseni Department of Chemistry, Islamic Azad University, Ahvaz Branch, Ahvaz, Iran.
Abstract:

The present study, for the first time, presents a feasible protocol for the preparation of β-cyclodextrin/ imidazolium based dicationic ionic liquid, [βCD/Im](OTs)2, and its application as an efficient and eco-friendly microvessel and host ionic liquid system for the regioselective ring opening of the epoxides in water. No evidence for the formation of diol by-products or side reactions, such as isomerization, epimerization and rearrangements was observed and 1,2-disubstituted products, β-azidoalcohols, β-cyanohydrins, and β-thiocyanohydrins, obtained in pure form. Short reaction time, easy reaction conditions, simple work-up procedure, high yield, reusability, and use of an eco-friendly catalyst are some of the striking features of the present protocol.  

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water

Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.

full text

Synthesis and Characterization of the Inclusion Complex of Dicationic Ionic Liquid and β-Cyclodextrin

The supramolecular structure of the inclusion complex of β-cyclodextrin (β-CD) with 1,1',2,2'-tetramethyl-3,3'-(p-phenylenedimethylene) diimidazolium dibromide (TetraPhimBr), a dicationic ionic liquid, has been investigated. The inclusion complex with 1:1 molar ratio was prepared by a kneading method. Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (XRD) analysis, (1)H ...

full text

One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids

In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easi...

full text

Conventional Study on Novel Dicationic Ionic Liquid Inclusion with β-Cyclodextrin

This study focuses on the synthesis and characterization of the inclusion complex of β-Cyclodextrin (β-CD) with dicationic ionic liquid, 3,3'-(1,4-Phenylenebis [methylene]) bis(1-methyl-1H-imidazol-3-ium) di(bromide) (PhenmimBr). The inclusion complex was prepared at room temperature utilizing conventional kneading technique. Proton ((1)H) NMR and 2D ((1)H-(1)H) COSY NMR were the primary charac...

full text

Si-Imidazole-HSO4 Functionalized Magnetic Fe3O4 Nanoparticles as an Efficient and Reusable Catalyst for the Regioselective Ring Opening of Epoxides in Water

An efficient and simple method for the preparation of Si-Imidazole-HSO4 functionalized magnetic Fe3O4 nanoparticles (Si-Im-HSO4 MNPs) and used as an efficient and reusable magnetic catalysts for the regioselective ring opening of epoxides under green conditions in water. This catalyst was used for the ring opening of epoxide corresponding to the thiocyanohydrins and azidohydrines. Compared to t...

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 7  issue 2

pages  153- 159

publication date 2017-06-01

By following a journal you will be notified via email when a new issue of this journal is published.

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023