Camphorpyrazolium-based chiral functional ionic liquids

Pastran J, Agrifoglio G, Gonzalez T, Briceno A, Dorta R (2014)

Publication Status: Published

Publication Type: Journal article

Publication year: 2014

Journal

Tetrahedron-Asymmetry Elsevier

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

Book Volume: 25

Pages Range: 1280-1285

Journal Issue: 18-19

DOI: 10.1016/j.tetasy.2014.07.014

Abstract

The solvent-less quaternization of N-phenyl-camphorpyrazole 4 with BrC4H9,IC2H4OCH3, and IC2H4OC2-H4OC4H9 afforded the corresponding chiral pyrazolium halides 5a, 6a, and 7a in excellent yields. The anions were modified either by trihalide formation with Br-2 and 12, or by salt metathesis with LiNTf2 and NaCo(CO)(4). All pyrazolium salts bearing the di-ether side chain 7a-d were liquids at room temperature, while the X-ray crystal structure of the bis(trifluoromethylsulfonyl)amide salt of the corresponding mono-ether analogue 6c (mp 97 degrees C) revealed intermolecular H-bonding interactions. Furthermore, an improved protocol for the well-known but notoriously low-yielding synthesis of (+)-hydroxymethylene-camphor 3 is disclosed. (C) 2014 Elsevier Ltd. All rights reserved.

Authors with CRIS profile

Romano Dorta Professur für Anorganische Chemie

Involved external institutions

Venezuelan Institute for Scientific Research / Instituto Venezolano de Investigaciones Científicas (IVIC) VE Venezuela, Bolivarian Republic of (VE) Universidad Simón Bolívar VE Venezuela, Bolivarian Republic of (VE)

How to cite

APA:

Pastran, J., Agrifoglio, G., Gonzalez, T., Briceno, A., & Dorta, R. (2014). Camphorpyrazolium-based chiral functional ionic liquids. Tetrahedron-Asymmetry, 25(18-19), 1280-1285. https://dx.doi.org/10.1016/j.tetasy.2014.07.014

MLA:

Pastran, Jesus, et al. "Camphorpyrazolium-based chiral functional ionic liquids." Tetrahedron-Asymmetry 25.18-19 (2014): 1280-1285.

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