Pastran J, Agrifoglio G, Gonzalez T, Briceno A, Dorta R (2014)
Publication Status: Published
Publication Type: Journal article
Publication year: 2014
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Book Volume: 25
Pages Range: 1280-1285
Journal Issue: 18-19
DOI: 10.1016/j.tetasy.2014.07.014
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.
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://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.
BibTeX: Download